58963-70-5Relevant articles and documents
The total synthesis of (±)-ginkgolide B
Crimmins, Michael T.,Pace, Jennifer M.,Nantermet, Philippe G.,Kim-Meade, Agnes S.,Thomas, James B.,Watterson, Scott H.,Wagman, Allan S.
, p. 8453 - 8463 (2000)
The total synthesis of the potent PAF antagonist ginkgolide B has been accomplished. The complex architecture of ginkgolide B which includes six rings, eleven stereogenic centers, ten oxygenated carbons, and four contiguous fully substituted carbons is a
Facile Synthesis of Chiral Arylamines, Alkylamines and Amides by Enantioselective NiH-Catalyzed Hydroamination
Meng, Lingpu,Yang, Jingjie,Duan, Mei,Wang, You,Zhu, Shaolin
supporting information, p. 23584 - 23589 (2021/09/28)
Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed by NiH catalysis with a simple bioxazoline ligand under mild conditions. A wide range of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by nitroarenes, hydroxylamines and dioxazolones, respectively as amination reagents. The chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.
Preparation method of (E)-3-(3-furyl) acrylic acid
-
Paragraph 0048-0071; 0080-0081, (2020/08/30)
The invention belongs to the technical field of medical intermediates, and provides a preparation method of a nalfurafine intermediate (E)-3-(3-furyl) acrylic acid. The method comprises the followingsteps: generating the nalfurafine intermediate (E)-3-(3-furyl) acrylic acid from a 3-substituted furan compound and an acrylate compound under the action of a catalyst; the method is mild in reactioncondition, simple and convenient to operate and high in reaction yield, and the obtained product is high in isomerization purity; a refining process and a waste liquid treatment process are avoided sothat the production cost is reduced, and the environmental protection pressure is reduced.
Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi
Chen, Dong-Dong,Zhang, Bing-Yu,Liu, Xiu-Xiu,Li, Xing-Qiang,Yang, Xin-Juan,Zhou, Le
supporting information, p. 1149 - 1153 (2018/03/05)
A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.
Intramolecular Didehydro-Diels-Alder Reaction for the Synthesis of Benzo- and Dihydrobenzo-Fused Heterocycles
Bober, Ashley E.,Proto, Justin T.,Brummond, Kay M.
supporting information, p. 1500 - 1503 (2017/04/13)
Using an intramolecular didehydro-Diels-Alder reaction, ene-yne substituted pyrroles, thiophenes, and furans afford functionalized indoles, benzothiophenes, and benzofurans and the corresponding dihydroaromatic products. Product selectivity for the aromatic or dihydroaromatic product is controlled by the reaction conditions, which vary depending upon the substrate.
Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in?vitro exploration for therapeutic potential against HeLa cancer cell lines
Lad, Nitin P.,Kulkarni, Sarang,Sharma, Rajiv,Mascarenhas, Malcolm,Kulkarni, Mahesh R.,Pandit, Shivaji S.
, p. 870 - 878 (2016/12/18)
A novel modification of piperlongumine is designed, bearing a cyclic sulphonamide (sultam) and its synthesis is described. For the first time herein we report the synthesis and biological evaluation of the natural product derived cyclic sulfonamides using Grubbs second generation catalyst (Grubbs II) via ring closing metathesis approach. Synthesis of a series of piperlongumine derived sultams is done in a moderate to good yield using Wittig reaction, Ring-Closing Metathesis (RCM) and, amide synthesis by using mixed anhydride, approach. All synthesized compounds were evaluated for anticancer activity and some demonstrated dose dependent reduction in HeLa cell growth. Of these 7, 10 and 14 significantly reduced the cell growth. Consequently their calculated GI50values were found to be 0.1 or 0.1?μM.
Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates
Jiang, Xingyu,Hartwig, John F.
supporting information, p. 8887 - 8891 (2017/07/17)
Enantioselective allylic substitution with enolates derived from aliphatic esters under mild conditions remains challenging. Herein we report iridium-catalyzed enantioselective allylation reactions of silyl ketene acetals, the silicon enolates of esters, to form products containing a quaternary carbon atom at the nucleophile moiety and a tertiary carbon atom at the electrophile moiety. Under relatively neutral conditions, the allylated aliphatic esters were obtained with excellent regioselectivity and enantioselectivity. These products were readily converted into primary alcohols, carboxylic acids, amides, isocyanates, and carbamates, as well as tetrahydrofuran and γ-butyrolactone derivatives, without erosion of enantiomeric purity.
Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of N-Nosylhydrazones as Diazo Surrogate
Liu, Zhaohong,Liu, Binbin,Zhao, Xue-Feng,Wu, Yan-Bo,Bi, Xihe
supporting information, p. 928 - 932 (2017/02/15)
The cross-olefination reaction of donor and acceptor diazo compounds was explored. The use of N-nosylhydrazones as diazo surrogates and the dependence on silver catalysis were crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, and the functionalized alkene products were afforded in good to high yields with moderate (Z)/(E) selectivities. The experimental and DFT calculation results suggest that the cross-selectivity is due to selective activation of the silver catalyst for donor diazo compounds.
BF3·OEt2-mediated: Syn -selective Meyer-Schuster rearrangement of phenoxy propargyl alcohols for Z -β-aryl-α,β-unsaturated esters
Puri, Surendra,Hari Babu, Madala,Sridhar Reddy, Maddi
, p. 7001 - 7009 (2016/07/30)
Synthesis of Z-β-aryl-α,β-unsaturated esters from readily available 1-aryl-3-phenoxy propargyl alcohols is achieved via a BF3-mediated syn-selective Meyer-Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.
Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes
Dieckmann, Michael,Jang, Yun-Suk,Cramer, Nicolai
supporting information, p. 12149 - 12152 (2015/10/12)
The cyclopentadienyl (Cp) group is a very important ligand for many transition-metal complexes which have been applied in catalysis. The availability of chiral cyclopentadienyl ligands (Cpx) lags behind other ligand classes, thus hampering the investigation of enantioselective processes. We report a library of chiral CpxIrIII complexes equipped with an atropchiral Cp scaffold. A robust complexation procedure reliably provides CpxIrIII complexes with tunable counterions. In a proof-of-concept application, the iodide-bearing members are shown to be highly selective for enyne cycloisomerization reactions. The dehydropiperidine-fused cyclopropane products are formed in good yields and enantioselectivities.
