Abstract

p-Benzoquinone has been converted into the substituted cyclohexenone (11) in five steps and 33% overall yield by a Diels-Alder cycloaddition-cycloreversion approach in which anthracene functions as a protecting and stereodirecting group. The elaboration of (11) in four steps to the known epoxide (22) constitutes a formal total synthesis of 3-O-demethylfortamine (2).