Abstract

The first total synthesis of the marine natural product metachromin A was accomplished through a convergent synthesis amenable to the preparation of synthetic analogues. The main features of this synthesis are the introduction of the oxygenation at C 17 employing a Thiele acetoxylation reaction and a stereoselective Horner-Wadsworth-Emmons coupling of a nonstabilized phosphonate with a methyl ketone derivative to generate the required (E)-trisubstituted double bond.

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