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Modular total syntheses of mycolactone A/B and its [2H]-isotopologue
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-08-29 00:00:00 , DOI: 10.1039/c7ob01943b
Sarah Saint-Auret 1, 2, 3, 4, 5 , Hajer Abdelkafi 1, 2, 3, 4, 5 , Didier Le Nouen 5, 6, 7, 8 , Laure Guenin-Macé 5, 9, 10, 11 , Caroline Demangel 5, 9, 10, 11 , Philippe Bisseret 1, 2, 3, 4, 5 , Nicolas Blanchard 1, 2, 3, 4, 5
Affiliation  

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.

中文翻译:

Mycolactone A / B及其[ 2 H]-异聚体的模块式全合成

通过编排几个Pd催化的关键步骤,已实现了霉菌内酯A / B(溃疡分枝杆菌产生的外毒素)的模块化全合成。虽然这种途径导致及其差向异构体C12(4天然产物的混合物  1倍的比率),这是从生物活性观点来看无关紧要的。相较于先前报道的路线,该合成蓝图允许毒素的后期变形例中,由[22,22,22-的制备例举2 ħ 3 ] -mycolactone A / B。
更新日期:2017-09-20
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