Highly efficient stereocontrolled total synthesis of (+)-upial

被引：9

作者：

Takahashi, Kazunori ^{[1
]}

Watanabe, Masayuki ^{[1
]}

Honda, Toshio ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 01期

关键词：

intramolecular reactions; natural products; silanes terpenoids; total synthesis;

D O I：

10.1002/anie.200704423

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Dual benefit:(+)-Upial, isolated from the sponge Dysidea fragilis (Kaneohe Bay, Hawaii), as a nonisoprenoid sesquiterpene aldehyde lactone, was efficiently synthesized. The key step involved an intramolecular carbonyl-ene reaction, in which the stereocontrolled construction of a bicyclo[3.3.1]nonane ring with five asymmetric carbon centers and the facile introduction of the exo-methylene unit were achieved in a single step (see scheme). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：131 / 133

页数：3

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