A Total Synthesis of the Sesquiterpene Quinone Metachromin-A

Article abstract of DOI:10.1016/S0040-4039(00)76220-4

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 the oxygenation at C17 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.