%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