Synthesis of Octahydroperylene, the Framework of Altertoxin III

Abstract

AbstractRoutes to the framework of perylenequinone‐derived mycotoxins of the dihydroanthracene type are described. Starting with anthracene derivatives, attachment of C3 units at positions 9 and 10 and twofold cyclization would furnish the required pentacycle. Heck‐type couplings, SN2 additions of enolates, alkynyl and allyl additions turned out to be not successful, while addition of a Grignard reagent prepared from acetal‐protected 3‐bromopropionaldehyde to anthraflavic acid methyl ester, subsequent acetal cleavage, and Birch reduction furnished octahydroperylene in only four steps.