Recent Advances in Natural Products Synthesis Using Bifunctional Organocatalysts bearing a Hydrogen-Bonding Donor Moiety

被引:16
作者
Odagi, Minami [1 ]
Nagasawa, Kazuo [1 ]
机构
[1] Tokyo Univ Agr & Technol, Dept Biotechnol & Life Sci, 2-24-16 Naka Cho, Koganei, Tokyo 1848588, Japan
基金
日本学术振兴会;
关键词
Bifunctionality; Hydrogen-bonding Donor; Organocatalyst; Natural Product Synthesis; CARBON QUATERNARY STEREOCENTERS; ASYMMETRIC TOTAL-SYNTHESIS; ERGOT ALKALOIDS; CASCADE REACTIONS; RISHIRILIDE-B; CHEMISTRY; CONSTRUCTION; NARCICLASINE; DERIVATIVES; HALICLONIN;
D O I
10.1002/ajoc.201900459
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Organocatalysis is widely used for the asymmetric synthesis of natural products and pharmaceuticals, and bifunctional organocatalysts are particularly effective for controlling stereochemistry. Here, we present an overview of natural products syntheses involving bifunctional catalysts bearing a hydrogen-bonding donor moiety reported during the last five years.
引用
收藏
页码:1766 / 1774
页数:9
相关论文
共 79 条
[1]   The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis [J].
Abbasov, Mikail E. ;
Romo, Daniel .
NATURAL PRODUCT REPORTS, 2014, 31 (10) :1318-1327
[2]   Thiourea-Catalyzed Enantioselective Malonate Addition onto 3-Sulfonyl-3′-indolyl-2-oxindoles: Formal Total Syntheses of (-)-Chimonanthine, (-)-Folicanthine, and (+)-Calycanthine [J].
Babu, K. Naresh ;
Roy, Avishek ;
Singh, Manvendra ;
Bisai, Alakesh .
ORGANIC LETTERS, 2018, 20 (20) :6327-6331
[3]   Total Syntheses of Pyroclavine, Festuclavine, Lysergol, and Isolysergol via a Catalytic Asymmetric Nitro-Michael Reaction [J].
Bhunia, Subhajit ;
Chaudhuri, Saikat ;
Bisai, Alakesh .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (47) :11234-11238
[4]   Organic synthesis provides opportunities to transform drug discovery [J].
Blakemore, David C. ;
Castro, Luis ;
Churcher, Ian ;
Rees, David C. ;
Thomas, Andrew W. ;
Wilson, David M. ;
Wood, Anthony .
NATURE CHEMISTRY, 2018, 10 (04) :383-394
[5]   Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms [J].
Bueschleb, Martin ;
Dorich, Stephane ;
Hanessian, Stephen ;
Tao, Daniel ;
Schenthal, Kyle B. ;
Overman, Larry E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (13) :4156-4186
[6]   Recent Progress in the Chemistry of Daphniphyllum Alkaloids [J].
Chattopadhyay, Amit Kumar ;
Hanessian, Stephen .
CHEMICAL REVIEWS, 2017, 117 (05) :4104-4146
[7]   Biomimetic Total Syntheses of Clavine Alkaloids [J].
Chaudhuri, Saikat ;
Bhunia, Subhajit ;
Roy, Avishek ;
Das, Mrinal K. ;
Bisai, Alakesh .
ORGANIC LETTERS, 2018, 20 (01) :288-291
[8]   Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine [J].
Chen, Si-Kai ;
Ma, Wen-Qiang ;
Yan, Zhi-Bo ;
Zhang, Fu-Min ;
Wang, Shao-Hua ;
Tu, Yong-Qiang ;
Zhang, Xiao-Ming ;
Tian, Jin-Miao .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (32) :10099-10103
[9]   Synthesis of 2-Oxindoles Sharing Vicinal All-Carbon Quaternary Stereocenters via Organocatalytic Aldol Reaction [J].
De, Subhadip ;
Das, Mrinal Kanti ;
Roy, Avishek ;
Bisai, Alakesh .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) :12258-12274
[10]   Unified Approach to the Spiro(pyrrolidinyl-oxindole) and Hexahydropyrrolo[2,3-b]indole Alkaloids: Total Syntheses of Pseudophrynamines 270 and 272A [J].
De, Subhadip ;
Das, Mrinal Kanti ;
Bhunia, Subhajit ;
Bisai, Alakesh .
ORGANIC LETTERS, 2015, 17 (23) :5922-5925