Synthesis of β-Trimethylsilyloxythioethers and β-Hydroxythioethers by the Reaction of Epoxides with Aryl- and Alkylthiotrimethylsilanes

Abstract

As part of our research into methods for the synthesis of leukotrienes (LTC₄, LTD₄, and LTE₄)¹, important natural mediators of allergic asthma, we have sought to develop mild and stereo-selective procedures for the preparation of complex β-hydroxythio-ethers. We have recently described the reaction of the S-trimethylsilyl derivative of N-trifluoroacetylglutathione dimethyl ester with the highly reactive epoxide, leukotriene A₄, as a key step in the synthesis of LTC₄ ². We now wish to report on the general synthetic utility and some mechanistic aspects of this novel reaction.