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 '-keto-galactoside, followed by stereoselective double bond reduction.
Franchini
Laura
L
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, Via Saldini 50, 20133-Milano, Italy. laura.franchini@unimi.it
Compostella
Federica
F
Colombo
Diego
D
Panza
Luigi
L
Ronchetti
Fiamma
F
D000475:Alkenes / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013451:Sulfonic Acids / Q000737:chemistry*
D000475:Alkenes; D008055:Lipids; D013451:Sulfonic Acids