
TY  - JOUR
A1  - Eade, RA 
A1  - Mcdonald, FJ 
A1  - Simes, JJH 
T1  - Extractives of Australian timbers. XV. The synthesis of 7,4'-Di-O-methylbayin
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1975
VL  - 28
IS  - 9
SP  - 2011
EP  - 2018
KW  - 
UR  - https://doi.org/10.1071/CH9752011 
N2  - The reaction between 2,6-dimethoxyphenylmagnesium bromide and tetraacetyl-&#945;-D- glucosyl chloride gave mainly &#945;-D-glucopyranosyl-2,6-dimethoxybenzene (8) and the &#946;-isomer (9). The a-isomer (8) was readily converted by acids into the /?-isomer (9), whose structure was confirmed by comparison with authentic material prepared by the degradation of 7,4?-di-O-methylbayin. The reaction of the tetraacetate of (9) with acetyl chloride in the presence of anhydrous aluminium chloride gave 3-&#946;-D-glucopyranosyl-2-hydroxy-4-methoxyacetophenone (11). Condensation of (11) with p-methoxybenzaldehyde gave the chalcone (15) which, on reaction with selenium dioxide, formed 7,4?-di-O-methylbayin (8-C-&#946;-D- glucopyranosyl-7,4?-dimethoxyflavone) (5). 
ER  -

