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.
A range of structural variations on the tricarbocyclic core 2 of the anti-bacterial agent platencin 1, including those represented by compounds 14, 15, and 27, have been prepared and certain of these elaborated, through substrate-controlled enolate alkylation reactions, to analogues of the natural product. Preliminary biological evaluation of these analogues revealed that they are only weakly active anti-infective agents.
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