Modular total syntheses of mycolactone A/B and its [2 H]-isotopologue
S Saint-Auret, H Abdelkafi, D Le Nouen… - Organic & …, 2017 - pubs.rsc.org
S Saint-Auret, H Abdelkafi, D Le Nouen, L Guenin-Macé, C Demangel, P Bisseret…
Organic & Biomolecular Chemistry, 2017•pubs.rsc.orgA 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.
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.
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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