Total synthesis of sulfolipid-1.
Sulfolipid-1, a tetra-acylated sulfotrehalose from Mycobacterium tuberculosis, was isolated over 40 years ago. Being a main component of the mycomembrane of M. tuberculosis, its biosynthesis and function have been studied in depth, but the chemical synthesis of sulfolipid-1 has not been reported. The synthesis presented here is based on iterative catalytic asymmetric conjugate additions of methylmagnesium bromide for the preparation of the phthioceranic and hydroxyphthioceranic acid side chains, a double regioselective reductive ring-opening and a fivefold deprotection in the final step.
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, NL-9747 AG Groningen, The Netherlands. a.j.minnaard@rug.nl.
Danny
D
Geerdink
Adriaan J
AJ
Minnaard
D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000737:chemistry; D037521:Virulence Factors / Q000138:chemical synthesis* / Q000737:chemistry
D006017:Glycolipids; D037521:Virulence Factors; C009355:sulfolipid I