Sulfone-mediated total synthesis of (±)-lepadiformine

被引：53

作者：

Caldwell, John J. ^{[1
]}

Craig, Donald ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 15期

关键词：

aziridines; cyclization; pyrrolidines; sulfones; total synthesis;

D O I：

10.1002/anie.200604670

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Key steps in the total synthesis of the marine alkaloid (±)-lepadiformine (1) include regioselective opening of a spirocyclic aziridine ring with a sulfone-stabilized carbanion, cyclocondensation of the N,C dianion of the resulting γ-sulfonamidosulfone with an aldehyde, and highly stereoselective alkynylation by nucleophilic substitution of an aminal. SES = 2-(trimethylsilyl)ethylsulfonyl. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2631 / 2634

页数：4

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