Synthesis of evodionol and alloevodionol

Abstract

The Hoesch reaction with acetonitrile and 7-benzyloxy-5-methoxy-2,2- dimethyl-chroman (7) yields mainly 8-acetyl-7-benzyloxy-5-methoxy-2,2- dimethylchroman (9); subsequent debenzylation and dehydrogenation forms alloevodionol (2). Both the Hoesch reaction with acetonitrile on 5- methoxy-2,2-dimethylchroman-7-ol (12) and the methylation of 8-acetyl- 2,2-dimethylchroman-5,7-diol (15) yield dihydroalloevodionol (11), convertible into alloevodionol (2) by dehydrogenation. 6-Acetyl-2,2- dimethylchroman-5,7-diol (14) is benzylated at the C7 hydroxyl and methylation, debenzylation, and dehydrogenation lead to evodionol (1).