Radical Cyclization in Heterocycle Synthesis. 11.1 A Novel Synthesis of α, β-Disubstituted γ-Lactones via Sulfanyl Radical Addition-Cyclization Using Hydroximates as …

O Miyata, A Nishiguchi, I Ninomiya, K Aoe…

Index: Naito, Takeaki; Honda, Yuko; Miyata, Okiko; Ninomiya, Ichiya Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995 , # 1 p. 19 - 26

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Citation Number: 47

Abstract

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 α, β-disubstituted γ-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. ...