- Using unnatural protein fusions to engineer resveratrol biosynthesis in yeast and mammalian cells
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Resveratrol is a naturally occurring defense compound produced by a limited number of plants in response to stresses. Besides cardiovascular benefits, this health-promoting compound has been reported to extend life spans in yeasts, flies, worms, and fish. To biosynthesize resveratrol de novo, tyrosine ammonia lyase (TAL), 4-coumarate CoA-ligase (4CL), and stilbene synthase (STS) were isolated from Rhodobacter sphaeroides, Arabidopsis thaliana, and Vitis vinifera, respectively. Yeast cells expressing 4CL and STS produce resveratrol when fed with 4-coumaric acid, the substrate of 4CL. When a translational fusion protein joining 4CL and STS was used, yeast cells produced 15-fold more resveratrol than the cotransformed cells, suggesting that physical localization of 4CL and STS facilitate resveratrol production. When the resveratrol pathway was introduced into human HEK293 cells, de novo biosynthesis was detected, leading to intracellular accumulation of resveratrol. We successfully engineered an entire plant natural product pathway into a mammalian host. Copyright
- Zhang, Yansheng,Li, Song-Zhe,Li, Jia,Pan, Xiangqing,Cahoon, Rebecca E.,Jaworski, Jan G.,Wang, Xuemin,Jez, Joseph M.,Chen, Feng,Yu, Oliver
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- Resveratrol and arctigenin production from polydatin and arctiin respectively by a thermostable β-glucosidase from Thermotoga maritima
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For preparation of resveratrol and arctigenin from peanut hulls and arctium lappa fruits, respectively, a recombinant β-glucosidase (TmBglA) from hyperthermophile Thermotoga maritima was purified and characterized. The hydrolytic activity was the highest at 90 °C and pH 6.2 for arctiin with Km of 1.61 mM and kcat of 197.4 s?1, and 90 °C and 5.8 for polydatin with Km of 0.38 mM and kcat of 47.6 s?1. The enzyme produced 215.4 mg L?1 resveratrol and 355.7 mg L?1 arctigenin from 400 mg L?1 polydatin and 540 mg L?1 arctiin after 60 min of incubation at 80 °C, with capable of hydrolyzing up to 92.1 and 94.9% of polydatin and arctiin, respectively. The enzymatic hydrolysis of peanut hulls and fructus arctii displayed a conversion yield of 3.8 and 0.33 mg resveratrol and arctigenin per gram of substrate material flour, respectively. Of the reported β-glucosidase, TmBglA exhibited the highest thermostability, kcat, kcat/Km, and conversion productivity for hydrolyzing polydatin and arctiin, and has great potential applications in functional food and medicine production.
- Xue, Yemin,Zhang, Zonghui,Hou, Jingjing,Cao, Zhigang,Zhang, Lingxian,Lou, Fen,Xu, Puxu
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- An innovative biotransformation to produce resveratrol by: Bacillus safensis
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Resveratrol is considered as a potential food supplement, cosmetic ingredient and nutraceutical. In this study, resveratrol was produced by biotransformation successfully. In detail, a β-glucosidase producing strain was isolated and identified as Bacillus safensis, and it could convert polydatin to resveratrol efficiently and rapidly. Further research showed that the conversion rate to resveratrol reached 93.1% in 8 h at 37 °C. The production of resveratrol was confirmed by HPLC, LC-MS and 1H-NMR to identify its structure and it was verified to possess antibacterial properties especially against Escherchia coli. To illustrate the resveratrol transformation mechanism, several glucosidases from B. safensis CGMCC 13129 were expressed and analyzed. The results showed that BGL4 and BGL5 had higher transformation activity compared with other tested glucosidases. This research provides a novel approach to produce resveratrol, and would promote the application of resveratrol in health-promoting pharmaceutical and food products.
- Hu, Xiaoyan,Liu, Yexue,Li, Dengke,Feng, Wei,Ni, Hanmeng,Cao, Shan,Lu, Fuping,Li, Yu
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- Identification of metabolic pattern and bioactive form of resveratrol in human medulloblastoma cells
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Cancer preventive reagent trans-resveratrol is intracellularly biotransformed to different metabolites. However, it is still unclear whether trans-resveratrol exerts its biological effects directly or through its metabolite(s). This issue was addressed here by identifying the metabolic pattern and the bioactive form of resveratrol in a resveratrol-sensitive human medulloblastoma cell line, UW228-3. The cell lysates and condition media of UW228-3 cells with or without 100 μM resveratrol treatment were analyzed by HPLC and LC/MS which revealed (1) that resveratrol was chemically unstable and the spontaneous generation of cis-resveratrol reduced resveratrol's anti-medulloblastoma efficacy and (2) that resveratrol monosulfate was the major metabolite of the cells. To identify the bioactive form of resveratrol, a mixture-containing approximately half fraction of resveratrol monosulfate was prepared by incubating trans-resveratrol with freshly prepared rat brain lysates. Medulloblastoma cells treated by 100 μM of this mixture showed attenuated cell crisis. The overall levels of the three brain-associated sulfotransferases (SULT1A1, 1C2 and 4A1) were low in medulloblastoma cells in vivo and in vitro in comparison with that in human noncancerous and rat normal cerebella; resveratrol could more or less up-regulate the production of these enzymes in UW228-3 cells but their overall level was still lower than that in normal cerebellum tissue. Our study thus demonstrated for the first time that trans-resveratrol is the bioactive form in medulloblastoma cells in which the expression of brain-associated SULTs was down-regulated, resulting in the increased intracellular bioavailability and anti-medulloblastoma efficacy of trans-resveratrol.
- Shu, Xiao-Hong,Li, Hong,Sun, Zheng,Wu, Mo-Li,Ma, Jing-Xin,Wang, Jian-Min,Wang, Qian,Sun, Yuan,Fu, Yuan-Shan,Chen, Xiao-Yan,Kong, Qing-You,Liu, Jia
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- Synthesis and Evaluation as Prodrugs of Hydrophilic Carbamate Ester Analogues of Resveratrol
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Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is an unfulfilled promise for health care: its exploitation is hindered by rapid conjugative metabolism in enterocytes and hepatocytes; low water solubility is a serious practical problem. To advantageously modify the physicochemical properties of the compound we have developed prodrugs in which all or part of the hydroxyl groups are linked via an N-monosubstituted carbamate ester bond to promoieties derived from glycerol or galactose, conferring higher water solubility. Kinetic studies of hydrolysis in aqueous solutions and in blood indicated that regeneration of resveratrol takes place in an appropriate time frame for delivery via oral administration. Despite their hydrophilicity some of the synthesized compounds were absorbed in the gastrointestinal tract of rats. In these cases the species found in blood after administration of a bolus consisted mainly of partially deprotected resveratrol derivatives and of the products of their glucuronidation, thus providing proof-of-principle evidence of behavior as prodrugs. The soluble compounds largely reached the lower intestinal tract. Upon administration of resveratrol, the major species found in this region was dihydroresveratrol, produced by enzymes of the intestinal flora. In experiments with a fully protected (trisubstituted) deoxygalactose containing prodrug, the major species were the prodrug itself and partially deprotected derivatives, along with small amounts of dihydroresveratrol. We conclude that the N-monosubstituted carbamate moiety is suitable for use in prodrugs of polyphenols. (Chemical Equation Presented).
- Azzolini, Michele,Mattarei, Andrea,La Spina, Martina,Marotta, Ester,Zoratti, Mario,Paradisi, Cristina,Biasutto, Lucia
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- Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis
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The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.
- Babu, Reshma,Balaraman, Ekambaram,Midya, Siba P.,Subaramanian, Murugan,Yadav, Vinita
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p. 7552 - 7562
(2021/06/28)
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- Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
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A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.
- Zhang, Zhao,Zhang, Dejiang,Zhu, Longzhi,Zeng, Dishu,Kambe, Nobuaki,Qiu, Renhua
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supporting information
p. 5317 - 5322
(2021/06/28)
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- N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions
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A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.
- Li, Dan,Tian, Qingqiang,Wang, Xuetong,Wang, Qiang,Wang, Yin,Liao, Siwei,Xu, Ping,Huang, Xin,Yuan, Jianyong
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supporting information
p. 2041 - 2052
(2021/05/25)
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- A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation
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Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.
- Thiel, Niklas O.,Kaewmee, Benyapa,Tran Ngoc, Trung,Teichert, Johannes F.
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p. 1597 - 1603
(2020/02/05)
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- Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation
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Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.
- Jia, Xiaofan,Frye, Lucas I.,Zhu, Weihao,Gu, Shunyan,Gunnoe, T. Brent
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supporting information
p. 10534 - 10543
(2020/06/08)
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- Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium
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Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.
- Tomanová, Monika,Jedinák, Luká?,Canka?, Petr
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supporting information
p. 2621 - 2628
(2019/06/03)
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- Cobalt catalyzed stereodivergent semi-hydrogenation of alkynes using H2O as the hydrogen source
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Cobalt-catalyzed stereodivergent semi-hydrogenation of internal alkynes to alkenes is developed. The reaction proceeded through transfer hydrogenation under mild conditions using a base metal CoI2 as the catalyst, and H2O/MeOH as the hydrogen source with Zn as the reductant. The E/Z-selectivity of the product could be switched by changing the solvent and by inclusion/exclusion of a bidentate phosphine ligand (dppe). This method provides a simple and cost effective pathway for the synthesis of 1,2-dideuterioalkenes.
- Li, Kangkui,Khan, Ruhima,Zhang, Xuexin,Gao, Yang,Zhou, Yongyun,Tan, Heng,Chen, Jingchao,Fan, Baomin
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p. 5663 - 5666
(2019/05/21)
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- Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2
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A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.
- Landge, Vinod G.,Yadav, Vinita,Subaramanian, Murugan,Dangarh, Pragya,Balaraman, Ekambaram
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supporting information
p. 6130 - 6133
(2019/06/03)
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- Preparation method of resveratrol
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The invention belongs to the technical field of preparation of medicine key intermediates, and particularly relates to a preparation method of resveratrol. The synthesis and preparation method of theresveratrol comprises the following steps: a, taking 3, 5-dimethoxybenzyl alcohol and phosphorus tribromide as raw materials, and synthesizing 3, 5-dimethoxybenzyl bromide (a compound A); b, taking the compound A, triethyl phosphite and tetrabutylammonium bromide as raw materials, and synthesizing to obtain 3, 5-dimethoxy benzyl diethyl phosphate (a compound B); c, taking the compound B, dimethyldiamide, sodium hydride and anisaldehyde as raw materials, and carrying out a reaction to synthesize to obtain (E) 3, 4 ', 5-trimethoxystilbene (compound C); and d, using the compound C and pyridine hydrochloride as raw materials, carrying out a reaction to synthesize 3, 4, 5-trihydroxy-1, 2-stilbene, namely the resveratrol. The method has the characteristics of cheap and easily available raw materials, mild reaction conditions, simple operation, high yield and low cost, and is beneficial to industrial production.
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Paragraph 0032; 0033
(2019/12/29)
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- Novel resveratrol as well as derivative synthesis method and application thereof
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The invention belongs to the technical field of organic synthesis and discloses novel resveratrol as well as a derivative synthesis method and application thereof. A target product resveratrol is obtained by taking 3,5-disubstituted aniline I as a raw material through the steps of carrying out diazotization reduction to generate 3,5-disubstituted arylhydrazine II, carrying out acetylation to obtain acyl arylhydrazine III, carrying out Heck coupling under the common catalysis of transition metal palladium and copper to obtain a resveratrol derivative and finally carrying out deprotection. The invention provides an efficient synthesis method of the resveratrol. The acyl arylhydrazine is used as a novel arylation reagent and the resveratrol is stereoselectively synthesized under the catalysisof a transition metal catalyst. The method provided by the invention has the advantages of easiness for obtaining the raw material, simplicity in operation and high stereoselectivity and the invention can provides an efficient method for synthesizing the resveratrol and related derivatives.
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Paragraph 0065; 0072-0073
(2019/08/02)
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- Preparation method of resveratrol compound
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The invention provides a preparation method of a resveratrol compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: firstly, carryingout oxidation addition and reduction elimination reaction on alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and a metal catalyst to obtain alkoxy-substituted diacetophenone; then carrying out reduction, reverse elimination and selective debenzylation reaction on the alkoxy-substituted diacetophenone and the metal catalyst in a hydrogen atmosphere to obtain the resveratrol compound. In the preparation method, hydrogenation reduction, reverse elimination and selective debenzylation reaction can be achieved through a one-pot method, trans-olefin is directly obtained through thereaction, and the generation of isomers is avoided; the Lewis acid is removed from the source through the selective catalytic debenzylation of the reaction, so that the method has the advantage of high yield, and is an environment-friendly process. Experimental results show that the products obtained by the preparation method are trans-olefins, the purity can reach more than 99.5%, and the yieldis more than 80%.
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- Method for artificially synthesizing resveratrol
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The invention relates to a method for artificially synthesizing resveratrol. The method disclosed by the invention comprises the following steps: taking 3,5-dihydroxy benzaldehyde as a raw material, taking RS004 as a catalyst, carrying out a Wittig-Honor reaction with p-hydroxybenzyl trimethyl phosphate so as to obtain resveratrol, filtering, desolventizing, re-crystallizing and drying, thereby obtaining the refined resveratrol. According to the method disclosed by the invention, the catalytic activity is high, the Wittig-Honor reaction can be selectively catalyzed to tolerate phenolic hydroxyl groups in the substrate, and the catalyst RS004 can be recycled and regenerated, so that the cost is reduced; the involved Wittig-Honor reaction process has the advantages of being mild in reactioncondition, simple in after-treatment and slight in pollution; and compared with the previous process, the method disclosed by the invention has the advantages of being simple in process, mild in condition, capable of meeting the green chemistry concept, suitable for industrial production and the like.
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Paragraph 0025-0044
(2019/04/13)
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- COSMETIC COMPOSTION COMRPISING ACTIVE INGREDIENT PRECURSOR AND ENZYME FOR MAINTAIN CONSTANTLY CONCENTRATION OF SKIN ACTIVE SUBSTANCE
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PURPOSE: A cosmetic composition containing enzyme and precursor with an activity at low temperature is provided to promoter skin cell activation and to improve anti-wrinkling and elasticity. CONSTITUTION: A cosmetic composition contains an enzyme with an activity at 0°C-15°C and at least one precursor which produces an active ingredient by reaction with the enzyme. The enzyme is hydrolase such as lipase, choline esterase, phosphatase, dioxyribonuclease, carboxypeptidase, pepsin, trypsin, or chemotrypsin. The precursor is retinyl palmitate, tocopheryl acetate, or piceid. The cosmetic composition is used for anti-aging, skin moisturizing, or skin whitening. The active ingredient is retinol, tocopherol, or resveratrol.
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Paragraph 0051-0053
(2018/05/24)
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- Direct Wittig Olefination of Alcohols
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A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination products. By the strategy of simultaneously in situ generation of ylides and aldehydes, for the first time, alcohols are directly transferred to olefins with no need of prepreparation of either aldehydes or ylides. Thus, the di/monocontrollable olefination of diols is accomplished. This synthetically practical method has been applied in the gram-scale synthesis of pharmaceuticals, such as DMU-212 and resveratrol from alcohols.
- Li, Qiang-Qiang,Shah, Zaher,Qu, Jian-Ping,Kang, Yan-Biao
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p. 296 - 302
(2018/02/19)
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- O -Iodoxybenzoic acid mediated generation of aryl free radicals: Synthesis of stilbenes through C-C cross-coupling with β-nitrostyrenes
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The generation of an aryl free radicals in the presence of nitrostyrenes through a combination of aryl hydrazines and o-iodoxybenzoic acid led to the synthesis of stilbenes by forming a new carbon-carbon bond after subsequent elimination of a nitrosyl radical. The symmetrical and unsymmetrical stilbenes with excellent E-selectivity were synthesized in good yields, with advantages of broad substrate scope and transition metal free, mild reaction conditions, under an open atmosphere in a short reaction time. A free radical mediated mechanism was postulated and supported by radical trapping experiments. Application of the developed methodology is demonstrated through a simple, two step synthesis of resveratrol, a valuable stilbenoid for anticancer and neurological studies via its prodrug E-1,3-dimethoxy-5-(4-methoxystyryl)benzene.
- Wagh, Ganesh,Autade, Snehalata,Patil, Pravin C.,Akamanchi, Krishnacharya G.
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p. 3301 - 3309
(2018/03/06)
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- Synthesis method of resveratrol
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The invention discloses a synthesis method of resveratrol. The synthesis method comprises the steps of a preparation technology of 3,5-dibromo-4-aminotoluene, a preparation technology of 3, 5-dibromotoluene, a preparation technology of (E)-1,3-dibromo-5-(4-methoxy-styrene)benzene, a preparation technology of (E)-1,3-dimethoxy-5-(4-methoxy-styrene)benzene and a preparation technology of resveratrol. The synthesis method has the advantages of being low in raw material price, less in step, high in yield and suitable for scale production.
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Paragraph 0053; 0069; 0070; 0071
(2018/07/30)
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- Synthesis method of resveratrol
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The invention provides a synthesis method of resveratrol, and belongs to the technical field of natural product synthesis. The synthesis method comprises the following steps: with 3,5-dimethoxy benzoic acid as a raw material, generating 3,5-dimethoxy benzoyl chloride (12) through an acylating chlorination reaction; generating 3,5-dimethoxy benzamide (13) through an amidation reaction of the (12);generating 3,5-dimethoxyaniline (14) through a Hofmann degradation reaction of the (13); generating 3,5-dimethoxy iodobenzene (15) through a Sandmeyer reaction on the (14); generating 3,5,4'-trimethoxy diphenylethene (31) through a reaction between the (15) and p-methoxystyrene (23), and performing demethylation of the (31) to finally obtain resveratrol (1), wherein total yield is 23.3%. Accordingto the method, the adopted reagent is cheap and easily available, aftertreatment is simple, and two expensive intermediates for Heck reaction are synthesized by adopting cheap raw materials. A new synthesis method is provided for synthesizing resveratrol.
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Paragraph 0047; 0048
(2018/05/03)
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- Preparation method of resveratrol
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The invention discloses a preparation method of resveratrol. The preparation method comprises that (1), 3, 5-dimethoxybenzhydrol is chloroformed under the action of triphosgene to form 3, 5-dimethoxybenzyl chloride, (2), 3, 5-dimethoxybenzyl chloride reacts with triphenylphosphine to produce phosphorus ylide, (3), phosphorus ylide and p-methoxybenzaldehyde form a cis-trans-isomer mixture of 3, 4',5-trimethoxydistyrene under the action of lithium hydroxide, (4), 3, 4', 5-trimethoxystilbene, aluminum and iodine are added to acetonitrile, the mixture is cooled to the room temperature so that yellow solids are separated, the yellow solids are filtered, the filtrate acetonitrile is directly recovered and recycled, 6N hydrochloric acid and ethyl acetate are added into the filter cake, the mixture is stood for layering, wherein the water layer contains ethyl acetate extract, the organic phases are mixed, the organic phases are washed through a saturated salt solution, anhydrous sodium sulfate is dried and filtered, the solvent is removed in vacuum through a water pump, and the organic phase is recrystallized through ethanol and water so that resveratrol is obtained. The preparation method utilizes easily available raw materials, is easy to operate and control, is environmentally friendly, produces easily purified products, has a high yield and is suitable for industrial production.
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Paragraph 0044-0048; 0049-0051; 0053-0055
(2018/11/03)
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- Method for preparing resveratrol
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The invention relates to a method for preparing resveratrol. 4-hydroxycinnamic acid serves as an initial raw material. High yield can be obtained, pollution is slight, and reaction conditions are mild. The method is a novel method for well synthesizing resveratrol.
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Paragraph 0040; 0061; 0077; 0078
(2018/12/13)
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- An acid-stable β-glucosidase from Aspergillus aculeatus: Gene expression, biochemical characterization and molecular dynamics simulation
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β-Glucosidases hydrolyze terminal, non-reducing β-D-glucosyl residues and thereby release β-D-glucose. They have applications in the production of biofuels, beverages and pharmaceuticals. In this study, a β-glucosidase derived from Aspergillus aculeatus (BGLA) was expressed, characterized, and the molecular mechanism of its acid denaturation was comprehensively probed. BGLA exhibited maximal activity at pH 5.0–6.0. Its optimal temperature was 70 °C. Its enzyme activity was enhanced by Mg2+, Ca2+ and Ba2+, while Cu2+, Mn2+, Zn2+, Fe2+ and Fe3+ had a negative effect. BGLA showed activity on a broad range of substrates including salicin, cellobiose, arbutin, geniposide and polydatin. Finally, the acid-denaturation mechanism of BGLA was probed using molecular dynamics (MD) simulations. The results of simulation at pH 2.0 imply that the contact number, solvent accessible surface area and number of hydrogen bonds in BGLA decreased greatly. Moreover, the distance between the residues Asp280 and Glu509 that are part of the active site increased, which eventually destroyed the enzyme's catalytic activity. These MD results explain the molecular mechanism of acid denaturation of BGLA, which will greatly benefit the rational design of more acid-stable β-glucosidase variants in the future.
- Li, Yu,Hu, Xiaoyan,Sang, Jingcheng,Zhang, Ying,Zhang, Huitu,Lu, Fuping,Liu, Fufeng
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p. 462 - 469
(2018/08/03)
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- Selective synthesis of the resveratrol analogue 4,4′-dihydroxy-: Trans -stilbene and stilbenoids modification by fungal peroxygenases
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This work gives first evidence that the unspecific peroxygenases (UPOs) from the basidiomycetes Agrocybe aegerita (AaeUPO), Coprinopsis cinerea (rCciUPO) and Marasmius rotula (MroUPO) are able to catalyze the regioselective hydroxylation of trans-stilbene to 4,4′-dihydroxy-trans-stilbene (DHS), a resveratrol (RSV) analogue whose preventive effects on cancer invasion and metastasis have very recently been shown. Nearly complete transformation of substrate (yielding DHS) was achieved with the three enzymes tested, using H2O2 as the only co-substrate, with AaeUPO showing exceptionally higher total turnover number (200000) than MroUPO (26000) and rCciUPO (1400). Kinetic studies demonstrated that AaeUPO was the most efficient enzyme catalyzing stilbene dihydroxylation with catalytic efficiencies (kcat/Km) one and two orders of magnitude higher than those of MroUPO and rCciUPO, so that 4-hydroxystilbene appears to be the best UPO substrate reported to date. In contrast, the peroxygenase from the ascomycete Chaetomium globosum (CglUPO) failed to hydroxylate trans-stilbene at the aromatic ring and instead produced the trans-epoxide in the alkenyl moiety. In addition, stilbenoids such as pinosylvin (Pin) and RSV were tested as substrates for the enzymatic synthesis of RSV from Pin and oxyresveratrol (oxyRSV) from both RSV and Pin. Overall, lower conversion rates and regioselectivities compared with trans-stilbene were accomplished by three of the UPOs, and no conversion was observed with CglUPO. The highest amount of RSV (63% of products) and oxyRSV (78%) were again attained with AaeUPO. True peroxygenase activity was demonstrated by incorporation of 18O from H218O2 into the stilbene hydroxylation products. Differences in the number of phenylalanine residues at the heme access channels seems related to differences in aromatic hydroxylation activity, since they would facilitate substrate positioning by aromatic-aromatic interactions. The only ascomycete UPO tested (that of C. globosum) turned out to have the most differing active site (distal side of heme cavity) and reactivity with stilbenes resulting in ethenyl epoxidation instead of aromatic hydroxylation. The above oxyfunctionalizations by fungal UPOs represent a novel and simple alternative to chemical synthesis for the production of DHS, RSV and oxyRSV.
- Aranda, Carmen,Ullrich, René,Kiebist, Jan,Scheibner, Katrin,Del Río, José C.,Hofrichter, Martin,Martínez, Angel T.,Gutiérrez, Ana
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p. 2394 - 2401
(2018/05/23)
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- Medicinal composition containing resveratrol and being capable of inhibiting drug-resisting staphylococcus aureus
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The invention belongs to the field of pharmacy, and relates to compound 3, 4',5-trihydroxy-diphenyl (resveratrol) and applications of the compound 3, 4',5-trihydroxy-diphenyl (resveratrol) in preparing sensitivity enhancing medicines of methicillin-resistant staphylococcus aureus capable of resisting fluoroquinolones. The compound 3, 4',5- trihydroxy-diphenyl (resveratrol) is wide in distribution,at present, resveratrol has been found in plants of at least 21 families, 31 categories and 72 kinds, wherein the contents in grape, polygonum cuspidatum and peanut are relatively high, and no obvious toxic and side effects exist. The antibacterial test shows that the compound has the pharmacological activity of improving the sensitivity of the multidrug-resisting staphylococcus aureus for norfloxacin, especially aiming at the methicillin-resistant staphylococcus aureus SA1199B containing fluoroquinolones-resisting gene NorA, the MIC value of norfloxacin can be reduced by 16 times after the compound and norfloxacin are mixed for use, and further, the composition can be used for preparing antibiotic synergistic medicines.
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Paragraph 0032; 0037; 0038
(2018/05/16)
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- Effect of flexible linker length on the activity of fusion protein 4-coumaroyl-CoA ligase::stilbene synthase
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In order to elucidate the effect of flexible linker length on the catalytic efficiency of fusion proteins, two short flexible peptide linkers of various lengths were fused between Arabidopsis thaliana 4-coumaroyl-CoA ligase (4CL) and Polygonum cuspidatum stilbene synthase (STS) to generate fusion proteins 4CL-(GSG)n-STS (n ≤ 5) and 4CL-(GGGGS)n-STS (n ≤ 4). The fusion proteins were expressed in both Escherichia coli and Saccharomyces cerevisiae, and their bioactivities were tested in vitro and in vivo using purified proteins and engineered strains, respectively. The catalytic efficiency of the fusions decreased gradually with the increase of GSG or GGGGS repeats. In both engineered S. cerevisiae and E. coli in vivo experiments, the capacity of resveratrol production decreased gradually with increasing linker length. In silico analysis showed that the prediction of homology models of fusion proteins was consistent with the in vitro and in vivo results.
- Guo, Huili,Yang, Yadong,Xue, Feiyan,Zhang, Hong,Huang, Tiran,Liu, Wenbin,Liu, Huan,Zhang, Fenqiang,Yang, Mingfeng,Liu, Chunmei,Lu, Heshu,Zhang, Yansheng,Ma, Lanqing
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p. 598 - 606
(2017/03/09)
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- Active Ruthenium (0) Nanoparticles Catalyzed Wittig-Type Olefination Reaction
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Abstract: Five different Ru metal precursors were reduced in imidazolium based ionic liquids under hydrogen atmosphere (4?bar) at 50 °C to obtain well-dispersed and stable Ru nanoparticles. Transmission electron microscopy (TEM) analysis confirmed size of well dispersed ionic liquid mediated Ru particles (Ru NPs) of 5?nm (±0.5) in diameter. These ruthenium nanoparticles (in ionic liquids) were used for Wittig type olefination reaction under mild reaction environment (70 °C and 1?h). The corresponding stilbenes were obtained in good yield with low-average selectivity. The proposed methodology is especially efficient for the synthesis of stilbenes as they were synthesized in the absence of any additive (as a hydrogen acceptor). The new catalytic system was also successfully applied for the synthesis of polymethoxylated and polyhydroxylated stilbenes, including resveratrol and DMU-212. Graphical Abstract: [Figure not available: see fulltext.]
- Srivastava, Vivek
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p. 693 - 703
(2017/03/08)
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- Method for synthesizing artificially all-trans-resveratrol and derivative thereof
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The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.
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Paragraph 0026; 0027
(2017/08/31)
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- A method for the synthesis of hydroxy [...] composition of the new method (by machine translation)
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The present invention discloses a new method for the synthesis of hydroxy [...] compound. The claimed method is: in the organic solvent, under a certain temperature, ammonium formate/through the palladium catalytic removal of benzyl protecting group system, to obtain hydroxyl [...] compound. The method has the mild reaction conditions, the operation is simple, small reagent toxicity, safety, high yield, wide range of application, low cost, relatively suitable for mass production and the like. (by machine translation)
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Paragraph 0075-0076
(2017/08/27)
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- An expedient synthesis of resveratrol through a highly recoverable palladium catalyst
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A straightforward two-step synthesis of resveratrol is described, with total isolated yields in the range of 75–80%. The key synthetic step, a Heck–Mizoroki C[sbnd]C cross-coupling reaction, is efficiently promoted by a heterogeneous catalyst consisting of palladium nanoparticles supported on synthetic clay. This solid catalyst is quite handy and displays high stability and robustness under reaction conditions. The catalyst can be easily recovered and reused at least 10 times, which improves the overall catalytic efficiency of the system. Moreover, the use of solvents is limited, and the reaction procedure allows a facile separation and purification of the desired product, free from the concomitant ionic by-product and from palladium contamination.
- Martínez, Alejandro V.,García, José I.,Mayoral, José A.
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p. 5581 - 5584
(2017/08/26)
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- Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System
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The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.
- El-Deeb, Ibrahim Yussif,Funakoshi, Tatsuya,Shimomoto, Yuya,Matsubara, Ryosuke,Hayashi, Masahiko
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p. 2630 - 2640
(2017/03/14)
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- Synthesis method for preparing resveratrol
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The invention relates to the technical field of medicine, particularly a synthesis method for preparing resveratrol. The novel synthesis method of resveratrol comprises the following steps: 1) carrying out Heck coupling reaction; and 2) saponifying the compound (3), acidifying, and recrystallizing to obtain the target product compound (1). The green environment-friendly ligand-free Heck cross coupling reaction method is used for synthesizing the resveratrol. The novel synthesis method of resveratrol has the advantages of simple route, high total yield, low cost and convenient after-treatment. The method is not reported in documents, and has excellent industrial production prospects.
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Paragraph 0057; 0058; 0059
(2017/08/28)
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- Regioselective Hydroxylation of Stilbenes by Engineered Cytochrome P450 from Thermobifida fusca YX
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Since the past decades, the plant stilbenoid resveratrol has gained significant attention of the general public as well as the research community due to its versatile medicinal properties. Apart from resveratrol, there is also an increasing interest in other plant stilbenoids because of their different potential biological activities. In order to meet the increasing demand for stilbenoids, alternative and sustainable approaches for their production are needed. We identified the cytochrome P450 monooxygenase 154E1 from Thermobifida fusca YX (CYP154E1) which enables the synthesis of (E)-4,4′-dihydroxystilbene via direct double hydroxylation of (E)-stilbene. The construction of a triple mutant led to a more than six-fold increased catalytic efficiency compared to the wild type enzyme. CYP154E1 and variants thereof accepted not only (E)-stilbene but also possessed remarkable activity towards ortho- and meta-substituted hydroxystilbenes leading to resveratrol, (E)-2,4′-dihydroxystilbene, (E)-2,4′,5-trihydroxystilbene and (E)-3,4′-dihydroxystilbene. The combination of protein engineering and the use of methyl-β-cyclodextrin as substrate solubilizing agent resulted in product titers of up to 4.2 g L?1 and enzyme total turnover numbers (TTN) of up to 20,000. (Figure presented.).
- Rühlmann, Ansgar,Antovic, Dragutin,Müller, Thomas J. J.,Urlacher, Vlada B.
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p. 984 - 994
(2017/03/27)
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- Preparation method for health product resveratrol
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The invention provides a preparation method for a health product resveratrol. According to the invention, 1, a deprotection method used in the invention is green, environment-friendly and pollution-free, the preparation method is almost free of production of waste gas, waste water and industrial residues, and the product 1,4-pentadiene has economic value; 2, a catalyst used in the invention has good cycle repeatability and can be cyclically used 50 times or more; 3, the preparation method is simple in operation requirements, mild in reaction conditions, good in specificity, simple in post-treatment and purification of the product, and suitable for industrial production; and 4, the resveratrol prepared by using the method is free of impurity and has high purity.
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- Synthesis of trans-resveratrol using modified Julia olefination route
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Bioactive hydroxystilbinoid-trans-resveratrol [(E)-3,5,4′ trihydroxy stilbene, 1] has been synthesized by modified Julia olefination method. The reaction between corresponding carbanion of benzothiazol-2-yl sulfone derivative and p-anisaldehyde dimethyl acetal with sodium hydride as a base, affords mainly cis-3,5,4′ trimethoxystilbene 10b with minor quantity of trans-isomev. Both the isomers have been separated in pure form and confirmed by their NMR spectral data. Demethylation of cis-3,5,4′ trimethoxystilbene either with AlCVpyridine or AlCl3/triethylamine results in the formation of trans-resveratrol.
- Shenvi, Suvarna,Shivanna, Shivaprakash,Reddy, G. Chandrasekara
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p. 1035 - 1038
(2017/11/10)
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- A method for acetylation of resveratrol synthesis
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The invention discloses a method for synthesizing acetyl-trans-resveratrol. The method comprises the following steps: (1) using 3,4',5-trimethoxystilbene as a raw material, and adopting a complex prepared from aluminum trichloride and triethylamine as a demethylation reagentl; under the action of inorganic salt, and carrying out demethylating reaction so as to obtain trans-resveratrol; (2) under the action of triethylamine, carrying out acetylated reaction for the obtained trans-resveratrol and acetic anhydride so as to obtain the acetyl-trans-resveratrol. The method has the advantages of being high in yield, good in product quality, environment-friendly and low in cost, is suitable for industrialization, is simple in preparation, is suitable for industrialized operation, can reduce impurities, improves the product quality, and has a wide application prospect.
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Paragraph 0068-0069; 0071-0072; 0074-0075
(2020/02/08)
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- A facile and rapid access to resveratrol derivatives and their radioprotective activity
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A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes. The results revealed that some resveratrol derivatives efficiently protected the thymocytes from radiation-induced apoptosis.
- Uzura, Saori,Sekine-Suzuki, Emiko,Nakanishi, Ikuo,Sonoda, Motohiro,Tanimori, Shinji
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supporting information
p. 3886 - 3891
(2016/08/01)
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- Method for preparing resvertrol (by machine translation)
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The invention discloses method for preparing resvertrol, in order to 3,5-dimethoxy-methanol as the raw material, through chloropivaloyl, to obtain 3,5-dimethoxy oxygen radical chlorine animal pen, through the 3,5-dimethylbenzaldehyde by oxygen radical chlorine animal pen 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works. This invention, through the triphosgene 3,5-dimethoxy-methanol chloropivaloyl, instead of ethanol using sodium hydride and sodium, synthetic 3, the 4 [...], 5-trimethoxy stilbene, reuse alchlor and triethylamine so as to obtain crude product resveratrol methyl, then the ethanol and water is recrystallized to get resveratrol works, preparation method has high yield, low cost. (by machine translation)
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Paragraph 0029; 0030; 0031; 0032; 0033
(2016/10/31)
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- The carbonate derivatives as skin care
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Carbonates of anti-aging ingredients, in particular anti-oxidants and skin illuminating phenol ingredients, have been prepared as derivatives of these ingredients with enhanced physical properties. It has been demonstrated that these carbonates will hydrolyze under enzymatic catalysis to release the parent ingredient. In contrast, esters of the phenolic groups in many cases do not hydrolyze under the same conditions.
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Paragraph 0056; 0057
(2017/02/28)
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- Synthesis method of resveratrol
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The invention provides a synthesis method of resveratrol.The method includes the steps of dissolving 3,5-dihydroxybenzoic acid in solvent, conducting reaction on sodium borohydride and Lewis acid to obtain 3,5-dihydroxy-benzyl alcohol, conducting reaction on 3,5-dihydroxy-benzyl alcohol and triphenylphosphine hydrobromic acid in certain solvent to obtain corresponding phosphonium, and making the obtained phosphonium react with p-hydroxy benzaldehyde under the effect of strong alkali to directly obtain the product resveratrol.The preparation method includes few steps, precious metal catalysts are prevented from being used in protection and deprotection processes of phenolic hydroxyl groups in the technology, cost is low, operation is easy, reaction conditions are easy to achieve, and industrial production is facilitated.
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Paragraph 0030; 0035; 0036
(2016/12/01)
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- A new synthesis of resveratrol
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Resveratrol was synthesized in a 4-step synthesis using a simple Sonogashira type reaction with 93% yield using commercially available 3,5-dimethoxy-1-ethynyl-benzene and 4-iodoanisole, followed by reduction, isomerization, and deprotection and with an overall yield of 63%.
- Lara-Ochoa, Francisco,Sandoval-Minero, Leticia C.,Espinosa-Pérez, Georgina
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p. 5977 - 5979
(2015/10/28)
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- The application of template selectophores for the preparation of molecularly imprinted polymers
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Molecularly imprinted polymers are versatile materials with wide application scope for the detection, capture and separation of specific compounds present in complex feed stocks. A major challenge associated with their preparation has been the need to sacrifice one mole equivalent of the template molecule to generate the complementary polymer cavities that selectively bind the target molecule. Moreover, template molecules can often be difficult to synthesise, expensive or lack stability. In this study, we describe a new approach, directed at the use of synthetic selectophores, chosen as readily prepared and low cost structural analogues with recognition groups in similar three-dimensional arrangements as found in the target molecule. To validate the approach, a comparative study of selectophores related to the polyphenolic compound (E)-resveratrol has been undertaken using traditional and green chemical synthetic approaches. These molecular mimic compounds were employed as polymer templates and also as binding analytes to interrogate the recognition sites associated with the molecularly imprinted polymers. Importantly, the study confirms that the use of selectophores has the potential to confer practical advantages, including access to more efficient methods for selection and preparation of suitable template molecules with a broader range of molecular diversity, as well as delivering imprinted polymers capable of recognizing the target compound and structurally related products.
- Danylec, Basil,Schwarz, Lachlan J.,Harris, Simon J.,Boysen, Reinhard I.,Hearn, Milton T. W.
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p. 17601 - 17613
(2015/10/12)
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- PROCESS FOR THE PREPARATION OF POLYHYDROXYSTILBENE COMPOUNDS BY DEPROTECTION OF THE CORRESPONDING ETHERS
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A process for the preparation of polyhydroxystilbene compounds (particularly resveratrol, oxyresveratrol, piceatannol, gnetol and the like) by deprotection of the corresponding ethers using aluminium halide and a secondary amine is provided.
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Paragraph 0090; 0091; 0092; 0093
(2015/02/19)
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- Enzymatic formation of a resorcylic acid by creating a structure-guided single-point mutation in stilbene synthase
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A novel C17 resorcylic acid was synthesized by a structure-guided Vitis vinifera stilbene synthase (STS) mutant, in which threonine 197 was replaced with glycine (T197G). Altering the architecture of the coumaroyl binding and cyclization pocket of the enzyme led to the attachment of an extra acetyl unit, derived from malonyl-CoA, to p-coumaroyl-CoA. The resulting novel pentaketide can be produced strictly by STS-like enzymes and not by Chalcone synthase-like type III polyketide synthases; due to the unique thioesterase like activity of STS-like enzymes. We utilized a liquid chromatography mass spectrometry-based data analysis approach to directly compare the reaction products of the mutant and wild type STS. The findings suggest an easy to employ platform for precursor-directed biosynthesis and identification of unnatural polyketides by structure-guided mutation of STS-like enzymes.
- Bhan, Namita,Li, Lingyun,Cai, Chao,Xu, Peng,Linhardt, Robert J.,Koffas, Mattheos A. G.
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p. 167 - 173
(2015/05/13)
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- Selective deoxygenation of hydroxybenzaldehydes
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A method for selective deoxygenation of hydroxybenzaldehydes including, condensing syringaldehyde (3,5-dimethoxy-4-hydroxybenzaldehyde) and a functionalized phenylacetic acid with at least one first base and at least one anhydride to produce an arylcinnamic acid, decarboxylating of said arylcinnamic acid with at least one decarboxylation catalyst at temperatures ranging from about 30° C. to 200° C. or thermally at temperatures ranging from about 100° C. to 350° C. to produce a first stilbene, hydrodeoxygenating the stilbene by conversion to a sulfonate in the presence of at least one second base in water or at least one organic solvent to yield a sulfonate reducing the sulfonate(s) with a reductive elimination catalyst to produce a second stilbene, and reacting the second stilbene with a hydrolyzing agent to generate a polyphenol.
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Page/Page column 5; 11
(2015/01/07)
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- Recent advances of resveratrol in nanostructured based delivery systems and in the management of HIV/AIDS
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Resveratrol, a natural polyphenolic compound present in trees, in peanuts, in grapevines and exhibited multiple pharmacological activities. Extensive research in last two decades suggested that resveratrol possesses anti-inflammatory, anti-cancer, anti-viral, anti-amyloid, anti-arthritic and antioxidant properties. Some clinical reports have proposed that resveratrol might be a potential candidate for the prevention and/or treatment of HIV/AIDS and synergistically enhances the anti-HIV-1 activity. Resveratrol is not toxic to cells, and by itself reduces viral replication by 20% to 30%. With almost 12% of the world population suffering from HIV/AIDS including its resurgence in the developed world, better management of this global threat is highly desired. Further, various studies demonstrated several issues associated with resveratrol which account for its poor systemic bioavailability (almost zero) due to rapid and extensive first pass metabolism and existence of enterohepatic recirculation. In order to improve bioavailability and cellular uptake of resveratrol, various strategies have been adopted to date which includes resveratrol prodrug and the development of nanostructured delivery systems. Besides, nanostructured delivery systems are also known to inhibit the P-glycoprotein (P-gp) efflux, reduced metabolism by gut cytochrome P-450 enzymes, and circumnavigate the hepatic first-pass effect, facilitating absorption of drugs via intestinal lymphatic pathways. This review paper provides an updated bird's-eye view account on the publications and patents study on the recent novel approaches to deliver resveratrol in order to enhance oral bioavailability, overcome first pass metabolism and trounce enterohepatic recirculation to make resveratrol a therapeutically potent drug. Providing a relatively pithy overview, this paper thus presents recent advances of resveratrol for the treatment and prevention of HIV/AIDS.
- Singh, Gurinder,Pai, Roopa S.
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p. 178 - 188
(2015/01/08)
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- Acetal derivatives as prodrugs of resveratrol
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The pharmacological exploitation of resveratrol is hindered by rapid phase-II conjugative metabolism in enterocytes and hepatocytes. One approach to the solution of this problem relies on prodrugs. We report the synthesis and characterization as well as t
- Mattarei, Andrea,Azzolini, Michele,Carraro, Massimo,Sassi, Nicola,Zoratti, Mario,Paradisi, Cristina,Biasutto, Lucia
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p. 2781 - 2792
(2013/07/26)
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- CuI/1,10-phen/PEG promoted decarboxylation of 2,3-diarylacrylic acids: Synthesis of stilbenes under neutral and microwave conditions with an in situ generated recyclable catalyst
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A series of trans- or cis-stilbenes have been synthesized in good to excellent yields via a functional group-dependent decarboxylation process from the corresponding 2,3-diaryl acrylic acids in a neutral CuI/1,10-phen/PEG-400 system under microwave conditions. The in situ generation of the recyclable catalytic complex, the use of environmentally benign solvent PEG-400, the operational simplicity, the short reaction times, as well as the functional group-dependent chemo- and stereo-selectivity have made the decarboxylation process a highly efficient and applicable protocol.
- Zou, Yong,Huang, Qi,Huang, Tong-Kun,Ni, Qing-Chun,Zhang, En-Sheng,Xu, Tian-Long,Yuan, Mu,Li, Jun
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p. 6967 - 6974
(2013/10/08)
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- Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes
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4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.
- Schmidt, Bernd,Elizarov, Nelli,Berger, René,H?lter, Frank
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p. 3674 - 3691
(2013/06/27)
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