Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions?

Organic & Biomolecular Chemistry Pub Date: 2019-02-21 DOI: 10.1039/C9OB00324J

Abstract

Bioinspired sulfa-Michael/aldol cascade reactions have been developed for the semisynthesis of sulfur-containing heterocyclic derivatives of platensimycin and platencin, with three newly formed contiguous stereogenic centers. Density functional theory calculations revealed the mechanism for the stereochemistry control. This method was used in a synthesis of a platensimycin thiophene analogue with potent antibacterial activities against Staphylococcus aureus.

Graphical abstract: Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions
Recommended Literature