Radical cyclization in heterocycle synthesis.: 11.: A novel synthesis of α,β-disubstituted γ-lactones via sulfanyl radical addition-cyclization using hydroximates as a tether

被引：49

作者：

Miyata, O

Nishiguchi, A

Ninomiya, I

Aoe, K

Okamura, K

Naito, T ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe, Hyogo 6588558, Japan

[2] Tanabe Seiyaku Co Ltd, Analyt Res Lab, Osaka 5320031, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 21期

关键词：

D O I：

10.1021/jo000472w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A combination of sulfanyl radical addition-cyclization of dienes connected with hydroximates and subsequent conversion of the resulting cyclic hydroximate to the lactones provides a novel method for the construction of alpha,beta -disubstituted gamma -lactones. Upon treatment with thiophenol in the presence of AIBN, dienes connected-with hydroximates smoothly underwent sulfanyl radical addition-cyclization to give cyclic cis- and trans-hydroximates. Hydrolysis of cyclic hydroximates gave the desired cis- and trans-lactones in high yield. This method was successfully applied to the practical synthesis of (+/-)-oxo-parabenzlactone.

引用

页码：6922 / 6931

页数：10

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