Synthesis of chiral diether and tetraether phospholipids: regiospecific ring opening of epoxy alcohol intermediates derived from asymmetric epoxidation

DH Thompson, CB Svendsen, C Di Meglio…

Index: Thompson, David H.; Svendsen, Chris B.; Meglio, Ciro Di; Anderson, Valerie C. Journal of Organic Chemistry, 1994 , vol. 59, # 11 p. 2945 - 2955

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Citation Number: 28

Abstract

Diether and tetraether phospholipids have been synthesized using chiral epoxy alcohol starting materials (eg glycidol3-nitrobenzenesulfonate esters or tert-butyldiphenylsilyl ethers). These chiral precursors provide control over the stereochemistry, substitution patterns, and steric properties of the phosphoglycerol backbone. Configuration at the sn-2 glycerol carbon was controlled by asymmetric epoxidation of allyl alcohol followed by acid ...