Absolute conformation and chiroptical properties. VI. 2,2',3,3'- tetramethoxy-9,9'-bitriptycyl: A stereochemical analog of 1,2-disubstituted ethane with identical substituents

Article abstract of DOI:10.1246/bcsj.71.2715

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[5.2.1.0^1,5]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[5.2.1.0^1,5]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.