A Second-Generation Chemoenzymatic Total Synthesis of Platencin

Dedicated to Professor Steve Ley on the occasion of his 70^th birthday and in appreciation of the inspirational leadership he has provided to the discipline

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.

Key words

antibacterial - cross-coupling - cycloaddition - natural product - total synthesis

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