Modular total syntheses of mycolactone A/B and its [2H]-isotopologue
Sarah Saint-Auret1, Hajer Abdelkafi, Didier Le Nouen
1Université de Strasbourg, CNRS, Laboratoire de Chimie Moléculaire UMR 7509, 67000 Strasbourg, France. n.blanchard@unistra.fr.
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.
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