Synthesis of coleon C tri-O-methyl ether

Abstract

Starting from podocarpic acid, two model preparations are described leading to p-quinones suitably functionalized as intermediates in the synthesis of coleon C. The proper p-quinone was obtained by a regio- and stereo-selective route and, following steps previously found effective for the preparation of coleon U, a synthesis of tri-O-methyl coleon C has been achieved. Some of the by-products encountered have also been identified.