
%0 Journal Article
%A Lahey, FN 
%A Stick, RV 
%T Synthesis of evodionol and alloevodionol
%J Australian Journal of Chemistry
%D 1973/10/01
%V 26
%N 10
%P 2291-2295
%K 
%R https://doi.org/10.1071/CH9732291
%U https://www.publish.csiro.au/paper/CH9732291 
%X 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). 
