
TY  - JOUR
A1  - Lahey, FN 
A1  - Stick, RV 
T1  - Synthesis of evodionol and alloevodionol
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 10
SP  - 2291
EP  - 2295
KW  - 
UR  - https://doi.org/10.1071/CH9732291 
N2  - 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). 
ER  -

