
TY  - JOUR
A1  - Urban, S 
A1  - Capon, RJ 
T1  - Marine Sesquiterpene Quinones and Hydroquinones: Acid-Catalyzed Rearrangements and Stereochemical Investigations
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1994
VL  - 47
IS  - 6
SP  - 1023
EP  - 1029
KW  - 
UR  - https://doi.org/10.1071/CH9941023 
N2  - Acid treatment of both ilimaquinone (3) and 5-epi-ilimaquinone (9) yielded the same rearrangement products, (7) and (8), thus defining a common absolute stereochemistry. Likewise, acid- catalysed rearrangement of avarol (10) and arenarol (11) yielded the common product aureol (13), allowing the absolute stereochemistry of arenarol (11) and its related quinone  arenarone (12) to be assigned. This latter acid- catalysed rearrangement also yielded an unexpected electrophilic aromatic cyclization product (15), the dimethyl ether (17) of which could be obtained in quantitative yield from acid treatment of avarol  dimethyl ether (16). 
ER  -

