
TY  - JOUR
A1  - Cameron, DW 
A1  - Crosby, IT 
A1  - Feutrill, GI 
T1  - Synthesis of Ventilagone
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1992
VL  - 45
IS  - 12
SP  - 2025
EP  - 2035
KW  - 
UR  - https://doi.org/10.1071/CH9922025 
N2  - Synthesis of ventilagone (4) from the naphthol (5) was complicated by oxidation involving the central ring and by extensive epimerization to the trans series in the course of Lewis-acid-mediated demethylation . These complications were avoided by prior protection as the acetate (23). Oxidative demethylation and subsequent hydrolysis converted the latter into the dihydroxy quinone (6), which was also accessible from the nitro compound (26). Spectroscopic procedures for determining relative stereochemistry of such systems are discussed. Compound (6) underwent radical C-methylation to give ventilagone (4). 
ER  -

