
TY  - JOUR
A1  - Croft, JA 
A1  - Ritchie, E 
A1  - Taylor, WC 
T1  - Chemical studies of the Proteaceae. VIII. The conversion of grevillol into rapanone and experiments on the synthesis of ardisiaquinone A
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1976
VL  - 29
IS  - 9
SP  - 1979
EP  - 1987
KW  - 
UR  - https://doi.org/10.1071/CH9761979 
N2  - Oxidation of grevillol dimethyl ether gave 2-methoxy-6-tridecyl-1,4-benzoquinone which on Thiele-Winter acetoxylation afforded the triacetate of 5-methoxy-3-tridecylbenzene-1,2,4-triol. Hydrolysisfollowed by oxidation and demethylation then yielded rapanone.By the application of a known reaction sequence involving the Stevens rearrangement, dodec-6-ynedioic acid was converted into 5,5'-(hexadec-8-yne-1,16-diyl)diresorcinol tetramethyl ether which was similarly oxidized to the related diquinone. This substance could not be converted into ardisiaquinone A because Thiele-Winter acetoxylation was accompanied by attack on the triple bond.However, 5,5'-(hexadecane-l,l6-diyl)diresorcinol dimethyl ether by successive oxidation, acetoxylation, hydrolysis and oxidation gave dihydroardisiaquinone A. 
ER  -

