Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+ Complex

Org Lett. 2021 Jan 15;23(2):340-345. doi: 10.1021/acs.orglett.0c03850. Epub 2020 Dec 23.


The siderophore piscibactin is a key virulence factor involved in the iron uptake of pathogenic bacteria Photobacterium damselae subsp. piscicida and Vibrio anguillarum, responsible for the fish diseases photobacterioisis (pasteurellosis) and vibriosis, respectively. A convergent total synthesis of its Ga3+ complex using l-/d-cysteine as chiral agents and Meldrum's acid is described. A Staudinger reduction/Aza-Wittig process in the synthesis of the acid-sensitive β-hydroxy-2,4-disubstituted thiazoline moiety and the convenient protecting groups was a key step in this synthesis.

Publication types

  • Research Support, Non-U.S. Gov't