Highly efficient synthesis of tricyclic Amines by a cyclization/cycloaddition cascade: Total syntheses of aspidospermine, aspidospermidine, and quebrachamine

被引：82

作者：

Coldham, Iain

Burrell, Adam J. M.

White, Laura E.

Adams, Harry

Oram, Niall

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] Eli Lilly & Co, Lilly Res Ctr Ltd, Windlesham GU20 6PH, Surrey, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 32期

关键词：

alkaloids; amines; cyclization; cycloaddition; ylides;

D O I：

10.1002/anie.200701943

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Three in one: Three new rings can be made in one pot with complete control of the regio- and stereochemistry by a tandem cyclization/cycloaddition cascade reaction. Treatment of a chloroaldehyde with an amine gives a cyclic azomethine ylide that undergoes intramolecular cycloaddition onto a tethered alkene. The method was applied to the shortest known synthesis of aspidospermine (see scheme). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：6159 / 6162

页数：4

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