Radical cyclization in heterocycle synthesis. 11.(1) A novel synthesis of alpha,beta-disubstituted gamma-lactones via sulfanyl radical addition-cyclization using hydroximates as a tether

来自 ACS

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作者：

† Okiko Miyata，† Atsuko Nishiguchi，† Ichiya Ninomiya，‡ Keiichi Aoe，‡A Kimio Okamura，† Takeaki Naito

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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.

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