Showing papers by "Víctor S. Martín published in 1994"

Stereoselective synthesis of highly substituted γ-lactones and butenolides by intramolecular Michael addition of enantiomerically enriched γ-[(phenylthio)acyl]oxy α,β-unsaturated esters

Abstract: The synthesis of polysubstituted γ-lactones by the base-induced cycli- zation of enantiomerically enriched γ-[(phenylthio)acyl]oxy α,β-unsa- turated esters obtained from 2,3-epoxy alcohols is described. The pro- cedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final γ-lactone were synthesized with excellent stereoselectivity. Use- ful functional interconversions were successfully demonstrated, in par- ticular those resulting in butenolides