A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Abstract

A total synthesis of the potent antibacterial agent platencin is described. The reaction sequence used involves, as starting material, an enantiomerically pure cis-1,2-dihydrocatechol derived from the whole-cell biotransformation of iodobenzene. Simple chemical manipulations of this metabolite provide a triene that engages in a thermally promoted intramolecular Diels-Alder reaction to establish the octahydro-2H-2,4a-ethanonaphthalene core of platencin.