Synthesis of the sulfonate analogue of seminolipid via Horner-Wadsworth-Emmons olefination

The first synthesis of the sulfonate analogue of seminolipid,the main sulfoglycolipid in mammalian sperm, is reported. Installation of the sulfonate unit was accomplished by a quite unexplored strategy based on Horner-Wadsworth-Emmons olefination on a 3 0-keto-galactoside, followed by stereoselective double bond reduction.