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
收藏
页码：6922 / 6931
页数：10
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