%0 Journal Article %A Miyata, Okiko %A Nishiguchi, Atsuko %A Ninomiya, Ichiya %A Aoe, Keiichi %A Okamura, Kimio %A Naito, Takeaki %D 2000 %T 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 %U https://acs.figshare.com/articles/journal_contribution/Radical_Cyclization_in_Heterocycle_Synthesis_11_A_Novel_Synthesis_of_-Disubstituted_-Lactones_via_Sulfanyl_Radical_Addition_Cyclization_Using_Hydroximates_as_a_Tether/3685572 %R 10.1021/jo000472w.s001 %2 https://ndownloader.figshare.com/files/5775930 %K diene %K AIBN %K Novel Synthesis %K Radical Cyclization %K cyclic hydroximate %K lactone %K cyclic cis %K sulfanyl %K Heterocycle Synthesis %K cyclic hydroximates %K tran %K novel method %X 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. 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. %I ACS Publications