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Issue 18, 2014
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Total synthesis of sulfolipid-1

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Abstract

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

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Publication details

The article was received on 21 Oct 2013, accepted on 04 Jan 2014 and first published on 07 Jan 2014


Article type: Communication
DOI: 10.1039/C3CC48087A
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Citation: Chem. Commun., 2014,50, 2286-2288
  • Open access: Creative Commons BY license
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    Total synthesis of sulfolipid-1

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

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