Total synthesis of (+)-cylindricine C

被引：50

作者：

Arai, T ^{[1
]}

Abe, H ^{[1
]}

Aoyagi, S ^{[1
]}

Kibayashi, C ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 30期

关键词：

cylindricine; cyclic imine; Grignard reaction; azaspirocyclization; intramolecular Michael addition;

D O I：

10.1016/j.tetlet.2004.05.142

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective total synthesis of (+)-cylindricine C has been achieved starting with (S)-N-Boc-2-pyrrolidinone. The key elements of this synthesis involve the sequence of reactions including BF3-mediated addition of the allyl Grignard reagent to the cyclic imine, spirocyclization via enamine formation, and intramolecular Michael addition to form the tricyclic core. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5921 / 5924

页数：4

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