Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600

被引：243

作者：

Greshock, Thomas J. ^{[1
]}

Grubbs, Alan W. ^{[1
]}

Jiao, Ping ^{[2
]}

Wicklow, Donald T. ^{[3
,4
]}

Gloer, James B. ^{[2
]}

Williams, Robert M. ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

[2] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

[3] USDA ARS, Natl Ctr Agr Utilizat Res, Mycotoxin Res Unit, Peoria, IL 61604 USA

[4] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 19期

关键词：

biomimetic synthesis; Diels-Alder reaction; indoles; natural products; structure elucidation;

D O I：

10.1002/anie.200800106

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Stereochemically unique: A new prenylated indole alkaloid, (+)-versicolamide B, has been isolated from cultures of Aspergillus versicolor NRRL 35600. The structure has been assigned by 2D NMR experiments, and confirmed by a biomimetic total synthesis. Versicolamide B is the first member of the paraherquamide/stephacidin family of alkaloids found to possess the anti relative stereochemistry at C19. ent-Stephacidin A and ent-notoamide B were also isolated for the first time. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3573 / 3577

页数：5

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