A formal [3+3] cycloaddition approach to natural-product synthesis

被引：162

作者：

Hsung, RP ^{[1
]}

Kurdyumov, AV ^{[1
]}

Sydorenko, N ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 01期

关键词：

cyclization; cycloaddition; electrocyclic reactions; heterocycles; total synthesis;

D O I：

10.1002/ejoc.200400567

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A formal [3 + 3] cycloaddition strategy for constructing complex heterocycles is reviewed here. This formal cycloaddition involves condensation of alpha,beta-unsaturated iminium salts with 1,3-dicarbonyl equivalents. These reactions, consist of a Knoevenagel-type condensation followed by a reversible electron electrocyclic ring-closure. They constitute. a stepwise formal [3 + 3] cycloaddition protocol with the net result being the formation of two (alpha-bonds in addition to a new stereocenter adjacent to the heteroatom. This review describes in some detail, but not comprehensively, some precedents, problems, solutions, and stereochemical mechanistic issues, and focuses on applications of this formal cydoaddition strategy (C) Wiley-VCH Verlag GmbH & Co. KGwa, 69451 Weinheim, Germany, 2005)

引用

页码：23 / 44

页数：22

共 264 条

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