Issue 18, 2014

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.

Graphical abstract: Total synthesis of sulfolipid-1

Supplementary files

Article information

Article type
21 Oct 2013
04 Jan 2014
First published
07 Jan 2014
This article is Open Access
Creative Commons BY license

Chem. Commun., 2014,50, 2286-2288

Author version available

Total synthesis of sulfolipid-1

D. Geerdink and A. J. Minnaard, Chem. Commun., 2014, 50, 2286 DOI: 10.1039/C3CC48087A

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