Total synthesis of notholaenic acid

Abstract

Notholaenic acid (1). an inhibitor of photosynthesis isolated from ferns belonging to the genus Notholaena, was synthesized from 3-benzyloxy-2-bromo-5-methoxybenzyl alcohol. Oxidation to the analogous aldehyde followed by reaction with the phosphorane prepared from p-methoxybenzylbromide provided a mixture of Z and E stilbenes that was carboxylated by lithium-halogen exchange and treatment with carbon dioxide. Catalytic hydrogenation provided pure notholaenic acid (1). © 1985, American Chemical Society. All rights reserved.