307499-99-6Relevant academic research and scientific papers
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
Miyata, Okiko,Nishiguchi, Atsuko,Ninomiya, Ichiya,Aoe, Keiichi,Okamura, Kimio,Naito, Takeaki
, p. 6922 - 6931 (2007/10/03)
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.
