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

J Org Chem

Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133-Milano, Italy.

Published: August 2010

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 '-keto-galactoside, followed by stereoselective double bond reduction.

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http://dx.doi.org/10.1021/jo1008788DOI Listing

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