- Intramolecular [2 + 2] Cycloadditions of Alkyl(phenylthio)ketenes: Total Synthesis of (+)-Sphaerodiol
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Asymmetric total synthesis of (+)-sphaerodiol (2) has been achieved. A key step is an intramolecular [2 + 2] cycloaddition of alkyl(phenylthio)ketene for rapid assembly of the decalin ring.
- Wu, Xiang,Wang, Hai-Jun,Huang, Yong-Shuang,Li, Wei-Dong Z.
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Read Online
- Biomass to value added chemicals: Isomerisation of β-pinene oxide over supported ionic liquid catalysts (SILCAs) containing Lewis acids
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The isomerisation of β-pinene oxide was studied over supported ionic liquid catalysts (SILCAs) consisting of Lewis acids in immobilized ionic liquid. SILCAs were demonstrated as efficient catalysts for the transformation of β-pinene oxide to myrtanal with the product distribution and activity being dependent on the nature of the ionic liquid and Lewis acid strength of catalytic species. With the catalyst ZnCl2/[N(3-OH-Pr)Py][NTf2]/ACC, the highest myrtanal molar yield obtained was 68%.
- Salminen, Eero,Rujana, Luis,M?ki-Arvela, P?ivi,Virtanen, Pasi,Salmi, Tapio,Mikkola, Jyri-Pekka
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Read Online
- Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols
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By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.
- Shi, Chang-Yun,Yin, Liang,Zhang, Qi,Zhou, Si-Wei
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supporting information
p. 26351 - 26356
(2021/11/09)
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- New hybrid compounds combining fragments of usnic acid and monoterpenoids for effective tyrosyl-dna phosphodiesterase 1 inhibition
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Usnic acid (UA) is a secondary metabolite of lichens that exhibits a wide range of biological activities. Previously, we found that UA derivatives are effective inhibitors of tyrosyl-DNA phosphodiesterase 1 (TDP1). It can remove covalent complex DNA-topoisomerase 1 (TOP1) stabi-lized by the TOP1 inhibitor topotecan, neutralizing the effect of the drugs. TDP1 removes damage at the 3′ end of DNA caused by other anticancer agents. Thus, TDP1 is a promising therapeutic target for the development of drug combinations with topotecan, as well as other drugs for cancer treatment. Ten new UA enamino derivatives with variation in the terpene fragment and substituent of the UA backbone were synthesized and tested as TDP1 inhibitors. Four compounds, 11a-d, had IC50 values in the 0.23–0.40 μM range. Molecular modelling showed that 11a-d, with relatively short aliphatic chains, fit to the important binding domains. The intrinsic cytotoxicity of 11a-d was tested on two human cell lines. The compounds had low cytotoxicity with CC50 ≥ 60 μM for both cell lines. 11a and 11c had high inhibition efficacy and low cytotoxicity, and they enhanced topotecan’s cyto-toxicity in cancerous HeLa cells but reduced it in the non-cancerous HEK293A cells. This “protec-tive” effect from topotecan on non-cancerous cells requires further investigation.
- Dyrkheeva, Nadezhda S.,Filimonov, Aleksandr S.,Luzina, Olga A.,Zakharenko, Alexandra L.,Ilina, Ekaterina S.,Malakhova, Anastasia A.,Medvedev, Sergey P.,Reynisson, Jóhannes,Volcho, Konstantin P.,Zakian, Suren M.,Salakhutdinov, Nariman F.,Lavrik, Olga I.
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- One-Pot Absolute Stereochemical Identification of Alcohols via Guanidinium Sulfate Crystallization
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A novel technique for the absolute stereochemical determination of alcohols has been developed that uses crystallization of guanidinium salts of organosulfates. The simple one-pot, two-step process leverages facile formation of guandinium organosulfate single crystals for the straightforward determination of the absolute stereochemistry of enantiopure alcohols by means of X-ray crystallography. The strong hydrogen bonding network drives the stability of the crystal lattice and allows for a diverse range of organic alcohol substrates to be analyzed.
- Brummel, Beau R.,Lee, Kinsey G.,McMillen, Colin D.,Kolis, Joseph W.,Whitehead, Daniel C.
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supporting information
p. 9622 - 9627
(2019/12/02)
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- Perilla alcohol derivative and its preparation and use
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The invention belongs to the technical field of medicine, and relates to a series of perilla alcohol derivatives disclosed as Formula I, and preparation and application thereof. The invention also relates to pharmaceutically acceptable salts and solvates of the perilla alcohol derivatives, and a pharmaceutical composition containing the perilla alcohol derivatives or pharmaceutically acceptable salts thereof as active components, which can be used for treating cancers. The perilla alcohol derivatives and pharmaceutical salts thereof have favorable anticancer activity. The preparation method is simple and feasible, and is easy to operate.
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Paragraph 0025; 0026
(2018/04/02)
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- Perilla amine compound and its preparation and use (by machine translation)
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The invention belongs to the field of medical technology, involves a series of formula I structure perilla amine compound and its preparation and use. The states the perilla amine compound includes pharmaceutically acceptable salts and solvates, and states the perilla amines containing the compound or its pharmaceutically acceptable salt as an active ingredient of the composition, can be used for treating cancer. The invention the perilla amine compounds and their pharmaceutically acceptable salts has better anti-cancer activity, its preparation method is simple and feasible, and easy to operate. (by machine translation)
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Paragraph 0028; 0029
(2018/04/02)
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- Selective Base-free Transfer Hydrogenation of α,β-Unsaturated Carbonyl Compounds using iPrOH or EtOH as Hydrogen Source
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Commercially available Ru-MACHOTM-BH is an active catalyst for the hydrogenation of several functional groups and for the dehydrogenation of alcohols. Herein, we report on the new application of this catalyst to the base-free transfer hydrogenation of carbonyl compounds. Ru-MACHOTM-BH proved to be highly active and selective in this transformation, even with α,β-unsaturated carbonyl compounds as substrates. The corresponding aliphatic, aromatic and allylic alcohols were obtained in excellent yields with catalyst loadings as low as 0.1–0.5 mol % at mild temperatures after very short reaction times. This protocol tolerates iPrOH and EtOH as hydrogen sources. Additionally, scale up to multi-gram amounts was performed without any loss of activity or selectivity. An outer-sphere mechanism has been proposed and the computed kinetics and thermodynamics of crotonaldehyde and 1-phenyl-but-2-en-one are in perfect agreement with the experiment.
- Farrar-Tobar, Ronald A.,Wei, Zhihong,Jiao, Haijun,Hinze, Sandra,de Vries, Johannes G.
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supporting information
p. 2725 - 2734
(2018/02/28)
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- Hydrogenation and Reductive Amination of Aldehydes using Triphos Ruthenium Catalysts
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An air-stable and readily accessible ruthenium dihydride complex catalyses aldehyde hydrogenation under neutral conditions. A high activity has been shown in a number of examples, and solvent-free conditions are also applicable, which favours industrial-scale applications. The catalyst has also been demonstrated to be active at low catalyst loadings for the reductive amination of aldehydes under mildly acidic conditions. A number of examples of chemoselectivity challenges are also presented in which the catalyst does not reduce carbon?halogen groups, alkene or ketone functionality. The advantage of using the pre-formed complex, Triphos-Ru(CO)H2 (1), over in situ formed catalysts from Triphos and Ru(acac)3 (acac=acetylacetonate) is also shown in terms of both chemoselectivity and activity, in particular this can be seen if low reaction temperatures are used.
- Christie, Francesca,Zanotti-Gerosa, Antonio,Grainger, Damian
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p. 1012 - 1018
(2018/01/27)
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- Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives
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Two series of amino-modified derivatives of (S)-perillyl alcohol were designed and synthesized using (S)-perillaldehyde as the starting material. These derivatives showed increased antiproliferative activity in human lung cancer A549 cells, human melanoma A375-S2 cells and human fibrosarcoma HT-1080 cells comparing with that of (S)-perillyl alcohol. Among these derivatives, compounds VI5 and VI7 were the most potent agents, with the IC50s below 100 μM. It was demonstrated that the antiproliferative effect of VI5 was mediated through the induction of apoptosis in A549 cells.
- Hui, Zi,Zhang, Meihui,Cong, Lin,Xia, Mingyu,Dong, Jinhua
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p. 6671 - 6682
(2014/06/10)
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- General and highly efficient iron-catalyzed hydrogenation of aldehydes, ketones, and α,β-unsaturated aldehydes
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EnvIRONmentally friendly: The title hydrogenation of aldehydes, ketones, and α,β-unsaturated aldehydes is reported. In the presence of the catalyst 1, primary, secondary, and allylic alcohols were obtained in good to excellent yields under mild reaction conditions. The catalyst is easily and inexpensively prepared, and is also stable to air, water, and column chromatography. Copyright
- Fleischer, Steffen,Zhou, Shaolin,Junge, Kathrin,Beller, Matthias
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p. 5120 - 5124
(2013/06/27)
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- A molecularly defined iron-catalyst for the selective hydrogenation of α,β-unsaturated aldehydes
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A selective iron-based catalyst system for the hydrogenation of α,β-unsaturated aldehydes to allylic alcohols is presented. Applying the defined iron-tetraphos complex [FeF(L)][BF4] (L=P(PhPPh 2)3) in the presence of trifluoroacetic acid a broad range of aldehydes are reduced in high yields using low catalyst loadings (0.05-1 mol %). Excellent chemoselectivity for the reduction of aldehydes in the presence of other reducible moieties, for example, ketones, olefins, esters, etc. is achieved. Based on the in situ detected hydride species [FeH(H 2)(L)]+ a catalytic cycle is proposed that is supported by computational calculations. Copyright
- Wienh?fer, Gerrit,Westerhaus, Felix A.,Junge, Kathrin,Ludwig, Ralf,Beller, Matthias
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supporting information
p. 7701 - 7707
(2013/07/11)
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- Air-stable, nitrile-ligated (cyclopentadienone)iron dicarbonyl compounds as transfer reduction and oxidation catalysts
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A series of air-stable, nitrile-ligated (cyclopentadienone)iron dicarbonyl compounds was synthesized and their activities as catalysts in the transfer reduction of acetophenone were explored. While all were active catalysts, the acetonitrile adduct was chosen for further study and was found to be active in the transfer reduction of aldehydes and ketones and in the Oppenauer-type oxidation of secondary alcohols. The acetonitrile catalyst exhibited activities similar to those of an analogous air-sensitive iron hydride, but unlike the iron hydride it was unreactive in carbonyl reductions using hydrogen gas. Copyright
- Plank, Taylor N.,Drake, Jessica L.,Kim, Daniel K.,Funk, Timothy W.
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supporting information; experimental part
p. 597 - 601
(2012/05/04)
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- α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines
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A convenient synthesis of α,β-unsaturated imines requiring only an allylic alcohol, an amine and a Ru catalyst has been developed. The use of large excesses of oxidant and the purification of sensitive intermediates can be avoided.
- Rigoli, Jared W.,Moyer, Sara A.,Pearce, Simon D.,Schomaker, Jennifer M.
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supporting information; experimental part
p. 1746 - 1749
(2012/04/23)
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- PHARMACEUTICAL COMPOSITIONS COMPRISING MONOTERPENES
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The present invention provides a process for purifying a monoterpene or sesquiterpene having a purity greater than about 98.5% (w/w) The process comprises the steps of derivatizing the monoterpene (or sesquiterpene) to produce a monoterpene (or sesquiterpene) derivative, separating the monoterpene (or sesquiterpene) derivative, and releasing the monoterpene (or sesquiterpene) from the derivative Also encompassed by the scope of the present invention is a pharmaceutical composition comprising a monoterpene (or sesquiterpene) having a purity greater than about 98.5% (w/w) The purified monoterpene can be used to treat a disease such as cancer The present monoterpene (or sesquiterpene) may be administered alone, or may be co-administered with radiation or other therapeutic agents, such as chemotherapeutic agents.
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Page/Page column 39
(2011/10/03)
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- Radical reactions on pinene-oxide derivatives induced by Ti(III)
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A practical, brief and selective synthesis of several pinene oxide derived terpenoids can be achieved from readily available starting materials. The key step is a radical reaction promoted by titanocene chloride.
- Fernández-Mateos,Herrero Teijón,Rubio González
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supporting information; experimental part
p. 9529 - 9534
(2011/12/15)
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- Zinc-catalyzed chemoselective reduction of esters to alcohols
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Economical alcohols! A general and chemoselective catalytic reduction of esters to alcohols using inexpensive zinc acetate and silanes has been developed. The operational simplicity and the high functional group tolerance, without the need for protecting and deprotecting steps, make this procedure particularly attractive for organic synthesis. Copyright
- Das, Shoubhik,Moeller, Konstanze,Junge, Kathrin,Beller, Matthias
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experimental part
p. 7414 - 7417
(2011/08/05)
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- A candidate cDNA clone for (-)-limonene-7-hydroxylase from Perilla frutescens
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Cytochrome P450 mono-oxygenases from peppermint, spearmint and perilla (all members of the family Lamiaceae) mediate the regiospecific hydroxylation of the parent olefin (-)-limonene to produce essential oil components oxygenated at C3, C6 and C7, respectively. Cloning, expression and mutagenesis of cDNAs encoding the peppermint limonene-3-hydroxylase and the spearmint limonene-6-hydroxylase have allowed the identification of a single amino acid residue which determines the regiospecificity of oxygenation by these two enzymes. A hybridization strategy provided a cytochrome P450 limonene hydroxylase cDNA from perilla with which to further evaluate the structural determinants of regiospecificity for oxygenation of the common substrate (-)-limonene. The perilla cDNA was a partial clone of 1550 bp (lacking the N-terminal membrane insertion domain), and shared 66% identity with the peppermint 3-hydroxylase and spearmint 6-hydroxylase at the amino acid level. The perilla cytochrome P450 was expressed in Escherichia coli as a chimeric protein fused with the N-terminal membrane insertion domain of the limonene-3-hydroxylase. The kinetically competent recombinant protein was characterized and shown to produce a mixture of C3-, C6- and C7-hydroxylated limonene derivatives with a distribution of 33%, 14% and 53%, respectively.
- Mau, Christopher J.D.,Karp, Frank,Ito, Michiho,Honda, Gisho,Croteau, Rodney B.
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experimental part
p. 373 - 379
(2010/06/12)
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- Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones
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This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3·Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested.
- Santos Pisoni, Diego dos,Sobieski da Costa, Jessé,Gamba, Douglas,Petzhold, Cesar Liberato,César de Amorim Borges, Antonio,Ceschi, Marco Antonio,Lunardi, Paula,Saraiva Gon?alves, Carlos Alberto
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scheme or table
p. 526 - 535
(2010/04/06)
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- A chemoenzymatic, preparative synthesis of the isomeric forms of p-menth-1-en-9-ol: Application to the synthesis of the isomeric forms of the cooling agent 1-hydroxy-2,9-cineole
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A preparative-scale synthesis of the four p-menth-1-en-9-ol isomers 2a-5a has been achieved by means of two chemoenzymatic processes. Both synthetic pathways start from the enantiomeric forms of limonene that are converted into p-mentha-1,8-dien-9-al isomers 12 and 15. The baker's yeast mediated reduction of the latter aldehydes afforded compounds 3a and 5a, respectively, with very high enantioselectivity. Moreover, chemical reduction of 12 and 15 gives the mixtures of enantiopure diastereoisomers 2a/3a and 4a/5a, respectively. PPL (Porcine pancreas lipase) mediated resolution of the latter mixtures followed by fractionating crystallization of derivatives 2b-5b allowed the enantio- and diastereoisomerically pure alcohols 2a-5a to be obtained. Compounds 2a-5a have then been used as starting materials for the preparation of four isomers of the cooling agent 1-hydroxy-2,9-cineole (6-9). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Serra, Stefano,Fuganti, Claudio,Gatti, Francesco G.
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experimental part
p. 1031 - 1037
(2009/04/05)
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- Opening of epoxide rings catalyzed by niobium pentachloride
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The behavior of several epoxides when treated with NbCl5 was studied. In general, the studied epoxides reacted rapidly with NbCl5, giving, in most cases, more than one product (chlorohydrins, products containing solvent residues, as well as rearrangement products). A detailed study was performed to verify the effects of the temperature (rt, 0°C, or -78°C) and of the NbCl5 molar concentration on the composition of the products, yield, and time required for the reactions. Copyright Taylor & Francis Group, LLC.
- Constantino, Mauricio Gomes,Lacerda Jr., Valdemar,Invernize, Paulo Roberto,Filho, Luiz Carlos Da Silva,Da Silva, Gil Valdo Jose
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p. 3529 - 3539
(2008/03/13)
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- Reactions of allyl alcohols of the pinane series and of their epoxides in the presence of montmorillonite clay
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The reactivity of allyl alcohols of the pinane series and of their epoxides in the presence of montmorillonite clay in intra- and intermolecular reactions was studied. Mutual transformations of (+)-trans-pino-carveol ((+)-2) and (-)-myrtenol ((-)-3a) were major reactions of these compounds on askanite-bentonite clay (Schemes 1 and 2). However, the two reactions gave different isomerization products, indicating that the reactivity of the starting alcohol (+)-2 or (-)-3a was different from that of the same compound (+)-2 or (-)-3 formed in the course of the reactions, (-)-cis- and (+)-trans-Verbenol ((-)-16 and (+)-12, resp.), as well as (-)-cis-verbenol epoxide ((-)-20) reacted with both aliphatic and aromatic aldehydes on askanite-bentonite clay giving various heterocyclic compounds (Schemes 4, 5 and 7); the reaction path depended on the structure of both the terpenoid and the aldehyde.
- Il'ina, Irina V.,Volcho, Konstantin P.,Korchagina, Dina V.,Barkhash, Vladimir A.,Salakhutdinov, Nariman F.
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p. 353 - 368
(2008/02/08)
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- Stereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde
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A study on the regioselective reduction of the conjugate double bond of perillaldehyde is described. The chemical reduction of this substrate was investigated in order to provide a straightforward access to the relevant natural flavour, dihydroperillaldehyde. The biological reduction of both natural (S)-(-)-perillaldehyde and synthetic (R)-(+)-perillaldehyde was accomplished by means of fermenting baker's yeast. The latter microorganism converted, with different diastereoselectivity, the (S)- and (R)-enantiomers into the corresponding trans and cis saturated alcohols, respectively. The origin of the hydrogen atoms added to the double bond was studied by deuterium labelling experiments and 2H NMR measurements that clearly demonstrate a different mechanism of the biohydrogenation of the two enantiomeric forms of perillaldehyde.
- Fronza, Giovanni,Fuganti, Claudio,Pinciroli, Matteo,Serra, Stefano
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p. 3073 - 3077
(2007/10/03)
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- Sex differences in the metabolism of (+)- and (-)-limonene enantiomers to carveol and perillyl alcohol derivatives by cytochrome P450 enzymes in rat liver microsomes
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(+)-Limonene is reported to cause nephropathy in male rats, but not in female rats and other species of animals including mice, rabbits, guinea pigs, and dogs. Male rats contain high levels of α2u-globulin in kidneys, and it has been shown that limonene a
- Miyazawa, Mitsuo,Shindo, Masaki,Shimada, Tsutomu
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- Highly chemoselective catalytic hydrogenation of unsaturated ketones and aldehydes to unsaturated alcohols using phosphine-stabilized copper(I) hydride complexes
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A base metal hydrogenation catalyst composed of the phenyldimethylphosphine-stabilized copper(I) hydride complex provides for the highly chemoselective hydrogenation of unsaturated ketones and aldehydes to unsaturated alcohols, including the regioselective 1,2-reduction of α,β- unsaturated ketones and aldehydes to allylic alcohols. The active catalyst can be derived in situ by phosphine exchange using commercial [(Ph3P)CuH]6 or from the reaction of copper(l) chloride, sodium tert-butoxide, and dimethylphenylphosphine under hydrogen. The catalyst derived from 1,1,1- tris(diphenylphosphinomethyl)ethane is mechanistically interesting but less synthetically useful. (C) 2000 Elsevier Science Ltd.
- Chen, Jian-Xin,Daeuble, John F.,Brestensky, Donna M.,Stryker, Jeffrey M.
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p. 2153 - 2166
(2007/10/03)
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- Aminoborohydrides. 4. The Synthesis and Characterization of Lithium Aminoborohydrides: A New Class of Powerful, Selective, Air-Stable Reducing Agents
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Lithium aminoborohydrides (LiABH3) are a new class of powerful yet selective reducing agents that reproduce, in air, virtually all of the transformations for which lithium aluminum hydrides is now used.LiABH3's can be readily prepared as solids or generated in situ, are nonpyrophoric, and liberate hydrogen only slowly with protic solvents above pH 4.LiABH3's can be handled in dry air as easily as sodium borohydride and retain their chemical activity for at least 6 month when stored under nitrogen or dry air at 25 deg C.LiABH3's can be synthesized from any primary or secondary amine, thus allowing control of the steric and electronic environment of these reagents.
- Fisher, Gary B.,Fuller, Joseph C.,Harrison, John,Alvarez, Salvador G.,Burkhardt, Elizabeth R.,et al.
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p. 6378 - 6385
(2007/10/02)
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- Photochemically-Removable Silyl Protecting Groups
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(Hydroxystyryl)dimethylsilyl (HSDMS) and (hydroxystyryldiisopropylsilyl (HSDIS) reagents have been developed that readily protect primary and secondary alcohols and can be removed on irradiation with short wavelength light in polar solvent.
- Pirrung, Michael C.,Lee, Yong Rok
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p. 6961 - 6963
(2007/10/02)
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- Enantioselective synthesis of chiral liquid crystalline compounds from monoterpenes
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Chiral liquid crystalline compounds 1-9 have been synthesized enantioselectively from monoterpenes. The optical purities of (S)-(-)- and (R)-(+)-perillalcohol (16, 27), (S)-(-)- and (R)-(+)-1-pentyl-4-hydroxymethyl-1-cyclohexene (33, 34) and (2S,5S)-2-pentyl-5-hydroxymethyl-1-cyclohexanone (53) have been determined by 1H NMR analysis using chiral shift reagents. The mesomorphic phases and transition temperatures of compounds 2,3,5,6,7,8 and 9 have been characterized.
- Wang, Qian,Fan, Shi Yan,Wong, Henry N. C.,Li, Zhong,Fung, Bing M.,Twieg, Robert J.,Nguyen, Huu Tinh
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p. 619 - 638
(2007/10/02)
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- BIOTRANSFORMATION OF LIMONENE AND RELATED COMPOUNDS BY ASPERGILLUS CELLULOSAE
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The biotransformation of (+)-, (-)- and (+/-)-limones by Aspergillus cellulosae M-77 has been investigated. (+)-Limonene was transformed mainly to (+)-isopiperperitenone, (+)-limonene-1,2-trans-diol, (+)-cis-carveol and (+)-perilly alcohol, along with the minor formation of isopiperitenol and α-terpineol, whereas (-)-limonene was transformed to (-)-perillyl alcohol, (-)-limonene-1,2-trans-diol and (+)-neodihydrocarveol as the major products, along with the minor products such as (-)-isopiperitenone.In the case of the DL-form, perillyl alcohol, limonene-trans-1,2-diol, isopiperitenone and α-terpineol were also formed. 1-Methylcyclohexene and cyclohexene were also transformed to 3-methyl-2-cyclohexenone and 2-cyclohexenone via the corresponding alcohols, respectively.Key Word Index: Aspergillus cellulosae; biotransformation; (+)-, (-)- and (+/-)-limones; isoperitenone; limonene-1,2-trans-diol; cis-carveol; α-terpineol; 1-methylcyclohexene; cyclohexene; 3-methyl-2-cyclohexenone; 2-cyclohexenone.
- Noma, Yoshiaki,Yamasaki, Sumika,Asakawa, Yoshinori
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p. 2725 - 2728
(2007/10/02)
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- Synthese von (-)-Spathulenol
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In reference to the famous synthesis of (-)-aromadendrene, the synthesis of (-)-spathulenol (31) and (-)-7-epi-spathulenol (32) from (-)-β-pinene via (-)-perillaaldehyde and the intermediates 7, 19 and 25 is described.
- Surburg, Horst,Mondon, Albert
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p. 118 - 131
(2007/10/02)
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