Saint-Auret Sarah, Abdelkafi Hajer, Le Nouen Didier, Guenin-Macé Laure, Demangel Caroline, Bisseret Philippe, Blanchard Nicolas
Université de Strasbourg, CNRS, Laboratoire de Chimie Moléculaire UMR 7509, 67000 Strasbourg, France.
Org Biomol Chem. 2017 Sep 20;15(36):7518-7522. doi: 10.1039/c7ob01943b.
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-H]-mycolactone A/B.
通过精心安排几个钯催化的关键步骤，实现了溃疡分枝杆菌产生的外毒素——分枝杆菌内酯A/B的模块化全合成。虽然这条路线得到的是天然产物及其C12差向异构体的混合物（比例为4:1），但从生物活性的角度来看，这无关紧要。与先前报道的路线相比，这种合成方案允许对毒素进行后期修饰，以[22,22,22-H]-分枝杆菌内酯A/B的制备为例。
