Total synthesis of (±)-symbioimine

被引：27
作者：
Varseev, Georgy N. [1 ]
Maier, Martin E. [1 ]
机构：
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 29期
关键词：
alkaloids; cycloaddition; Diels-Alder reaction; imines;
D O I：
10.1002/anie.200601418
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) An inside job: A Lewis acid induced intramolecular Diels-Alder (IMDA) reaction is used as the key step in the formation of symbioimine, an iminium alkaloid. The intermediate octahydronaphthalene is obtained from the IMDA reaction, after which extension of the aldehyde to a nitrile, alkylation of the nitrile, and imine formation allows for an efficient route to the target compound (see scheme; TBS = tert-butyldimethylsilyl). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：4767 / 4771
页数：5
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