Total Synthesis of Cyanobactin Natural Product Balgacyclamide B.
Chemistry
; 30(3): e202303316, 2024 Jan 11.
Article
en En
| MEDLINE
| ID: mdl-37926692
ABSTRACT
Balgacyclamide A-C are a family of cyanobactin natural products isolated from freshwater cyanobacteria Microcystis aeruginosa. These macrocyclic peptides are characterized by their oxazoline-thiazole core, their 7 or 8 stereocenters, and their antiparasitic activities. Balgacyclamide B is known for its activity towards Plasmodium falciparum chloroquine-resistant strain K1, Trypanosoma brucei rhodesiense, and Leishmania donovani. In this report, the first total synthesis of Balgacyclamide B is described in a 17-steps pathway and a 2 % overall yield. The synthetic pathway toward balgacyclamide B can be adapted for the future syntheses of balgacyclamide A and C. In addition, a brief history background of oxazolines syntheses is shown to emphasize the importance of the cyclization conditions used to interconvert or retain configuration of ß-hydroxy amides via dehydrative cyclization.
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Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Péptidos Cíclicos
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Leishmania donovani
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Antiparasitarios
Idioma:
En
Año:
2024
Tipo del documento:
Article