Quinoline alkaloids. Part IX. A partial asymmetric synthesis of orixine

Abstract

Oxidation of 2,4-dimethoxy-3-(3-methylbut-2-enyl)-7,8-methylenedioxyquinoline with (+)-peroxycamphoric acid furnished a (–)-epoxide which was converted via a (+)-secondary monoformate into the (+)-diol, orixine. The absolute stereochemistry of the alkaloid is discussed.