Bulletin of the Chemical Society of Japan p. 2715 - 2720 (1998)
Update date:2022-08-03
Topics:
Toyota, Shinji
Yasutomi, Akihiro
Kojima, Hiroharu
Igarashi, Yuko
Asakura, Mitsuhiro
Oki, Michinori
The title compound was prepared by addition of 4,5-dimethoxybenzyne to 9,9'-bianthryl. The rotational isomers, ap and ±sc, were separated by HPLC. The ±sc isomers were treated with sodium ethanethiolate to produce 3,3'- dihydroxy-2,2'-dimethoxy-9,9'-bitriptycyl, which was converted to the ester of ('S, 5R,7R)-4-[(2-carboxy)benzoyl]-3-thia-4- azatricyclo[5.2.1.01,5]decane 3,3-dioxide. The resulting diastereomers were separated by HPLC. The isomers were hydrolyzed and methylated with dimethyl sulfate to yield optically active 2,2',3,3'-tetramethoxy-9,9'- bitriptycyl. The absolute conformation of the tetramethoxy compound was determined by X-ray structure analysis of 3'-ester of (1S,5R, 7R)-4-(2- carboxybenzoyl)-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide derived from 3-hydroxy-2,2',3'-trimethoxy-9,9'-bitriptycyl, followed by hydrolysis and then methylation. The CD spectrum of Msc-2,2',3,3'-tetramethoxy-9,9'- bitriptycyl is reported.
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