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Modular total syntheses of mycolactone A/B and its [2H]-isotopologue

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Abstract

A modular total synthesis of mycolactone A/B, the exotoxin produced by Mycobacterium ulcerans, has been achieved through the orchestration of several Pd-catalyzed key steps. While this route leads to a mixture of the natural product and its C12 epimer (4 : 1 ratio), this was inconsequential from the biological activity standpoint. Compared to the previously reported routes, this synthetic blueprint allows the late-stage modification of the toxin, as exemplified by the preparation of [22,22,22-2H3]-mycolactone A/B.

Graphical abstract: Modular total syntheses of mycolactone A/B and its [2H]-isotopologue

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Publication details

The article was received on 04 Aug 2017, accepted on 25 Aug 2017 and first published on 29 Aug 2017


Article type: Communication
DOI: 10.1039/C7OB01943B
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Modular total syntheses of mycolactone A/B and its [2H]-isotopologue

    S. Saint-Auret, H. Abdelkafi, D. Le Nouen, L. Guenin-Macé, C. Demangel, P. Bisseret and N. Blanchard, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01943B

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