OXIDATIVE FREE-RADICAL CYCLIZATION OF ALLYLIC ALPHA-CHLOROMALONATES - SYNTHESIS OF (+/-)-AVENACIOLIDE

被引：31

作者：

SNIDER, BB

MCCARTHY, BA

机构：

[1] Department of Chemistry, Brandeis University, Waltham

来源：

TETRAHEDRON | 1993年 / 49卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(01)80213-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative free-radical cyclization of alpha-chloromalonate 9 with Mn(OAc)3.2H2O and Cu(OAc)2.H2O in acetic acid at 75-degrees-C provides 82% of lactones 10a and 10b. Hydroboration of 10 followed by oxidation affords acids 12, which are converted to avenaciolide precursor 15 in 32% overall yield from 9 by decarboxylation and cyclization.

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页码：9447 / 9452

页数：6

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