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

Organic & Biomolecular Chemistry
Lin QiuYong Huang

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.

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

M06
Gaussian09

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