Complex examples of the Dowd-Beckwith rearrangement: a free radical route to 2-oxabicyclo [3.3.0]octan-3,6-diones

被引：6

作者：

Hart, DJ ^{[1
]}

Havas, F ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA

来源：

COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE | 2001年 / 4卷 / 07期

基金：

美国国家卫生研究院;

关键词：

halolactonization; free radical rearrangement; tri-n-butylstannane; allyltri-n-butylstannane;

D O I：

10.1016/S1387-1609(01)01274-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of 8-iodooxabicyclo[3.2.1]octanes from substituted benzoic acids via a reductive alkylation-halolactonization sequence is described. These iodolactones were converted to 2-oxabicyclo[3.3.0]octane derivatives upon treatment with either allyltri-n-butylstannane or tri-n-butylstannane via a process that involves a Dowd-Beckwith rearrangement. The scope and limitations of this process are discussed. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.

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收藏

页码：591 / 598

页数：8

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