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À propos de : Radical Cyclization in Heterocycle Synthesis. 11. A NovelSynthesis of α,β-Disubstituted γ-Lactones via Sulfanyl RadicalAddition−Cyclization Using Hydroximates as a Tether        

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  • Radical Cyclization in Heterocycle Synthesis. 11. A NovelSynthesis of α,β-Disubstituted γ-Lactones via Sulfanyl RadicalAddition−Cyclization Using Hydroximates as a Tether
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  • A combination of sulfanyl radical addition−cyclization of dienes connected with hydroximates andsubsequent conversion of the resulting cyclic hydroximate to the lactones provides a novel methodfor the construction of α,β-disubstituted γ-lactones. Upon treatment with thiophenol in the presenceof AIBN, dienes connected with hydroximates smoothly underwent sulfanyl radical addition−cyclization to give cyclic cis- and trans-hydroximates. Hydrolysis of cyclic hydroximates gave thedesired cis- and trans-lactones in high yield. This method was successfully applied to the practicalsynthesis of (±)-oxo-parabenzlactone.
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