Allergenic α-Methylene-γ-lactones. General Method for the Preparation of β-Acetoxy- and β-Hydroxy-α-methylene-γ-butyrolactones from Sulfoxides. Application to the Synthesis of a Tuliposide B Derivative

Article abstract of DOI:10.1021/jo00319a020

A general synthesis of β-hydroxy-α-methylene-γ-butyrolactones , which is based on the sulfoxide-sulfenate rearrangement, is presented.Several β-acetoxy-α-methylene-γ-butyrolactones have been prepared and transformed into the β-hydroxy-derivatives through base hydrolysis.This synthesis has been applied to the first preparation of (tetraacetoxybenzyl)tuliposide B (22).