Reduction of Esters/Lactones to Ethers via Corresponding Carbothionyl Compounds

Abstract

During the work directed towards the total synthesis of a brevetoxin B analogue, the transformation of esters and lac-tones to the corresponding ethers was examined. Conversion of esters/lactones to their carbothionyl ester derivatives, followed by treatment with triphenylstannane in the presence of AIBN gave the reduced product ethers in good to excellent yields. Interestingly, the use of tributylstannane, under otherwise identical conditions, did not give acceptable yields of the product ethers. Isolation of th e reaction intermediates suggests that a two-step reductive mechanism involving radicals is in ope ration.