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

Sarah Saint-Auret; Hajer Abdelkafi; Didier Le Nouen; Laure Guenin-Macé; Caroline Demangel; Philippe Bisseret; Nicolas Blanchard

doi:10.1039/C7OB01943B

Journal articles

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

Sarah Saint-Auret ¹ Hajer Abdelkafi ¹ Didier Le Nouen ² Laure Guenin-Macé ³ Caroline Demangel ³ Philippe Bisseret ¹ Nicolas Blanchard ^{1, *}

* Corresponding author

1 LCM - Laboratoire de chimie moléculaire

2 COB - Chimie organique et bioorganique

3 Immunobiologie de l'Infection - Immunobiology of Infection

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 previously reported routes, this synthetic blueprint allows the late-stage modification of the toxin, as exemplified with the preparation of [22,22,22-2

Document type :

Journal articles

Domain :

Life Sciences [q-bio] / Biochemistry, Molecular Biology

Life Sciences [q-bio] / Toxicology

Complete list of metadata

Cited literature [3 references] Display Hide Download

https://hal-pasteur.archives-ouvertes.fr/pasteur-01666631
Contributor : Marie-Luce Kop <>
Submitted on : Monday, December 18, 2017 - 3:46:07 PM
Last modification on : Tuesday, May 25, 2021 - 5:38:01 PM

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

Identifiers

Collections

Citation

Export

Metrics

349

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

Identifiers

Collections

Citation

Export

Share

Metrics

349