Total Synthesis of Cyanobactin Natural Product Balgacyclamide B.

Autor: Torres-Hernandez AX; Department of Chemistry, Kansas State University, 1212 Mid-Campus Drive, 203 CBC, Manhattan, KS, 66506, USA., Desman P; Department of Chemistry, Kansas State University, 1212 Mid-Campus Drive, 203 CBC, Manhattan, KS, 66506, USA., Nguyen T; Department of Chemistry, Kansas State University, 1212 Mid-Campus Drive, 203 CBC, Manhattan, KS, 66506, USA., Hoang V; Department of Chemistry, Kansas State University, 1212 Mid-Campus Drive, 203 CBC, Manhattan, KS, 66506, USA., Zhang Y; Department of Chemistry, Kansas State University, 1212 Mid-Campus Drive, 203 CBC, Manhattan, KS, 66506, USA., Bartels A; Department of Chemistry, Kansas State University, 1212 Mid-Campus Drive, 203 CBC, Manhattan, KS, 66506, USA., Rafferty RJ; Department of Chemistry, Kansas State University, 1212 Mid-Campus Drive, 203 CBC, Manhattan, KS, 66506, USA.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jan 11; Vol. 30 (3), pp. e202303316. Date of Electronic Publication: 2023 Nov 21.
DOI: 10.1002/chem.202303316
Abstrakt: 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 β-hydroxy amides via dehydrative cyclization.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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