Abstract:
Four stereo-isomers of anisodamine were obtained by two consecutive resolutions. (+) 6-Methoxy methoxy tropinone (+Ⅰ) and its optical antipode (-Ⅰ) could be obtained by the resolution of racemic (Ⅰ) with (+) L-tartaric acid and (-) D-tartaric acid respectively. Subsequent catalytic hydrogenation of the optically active compound Ⅰ, then ester exchange with methyl 2-formyl-2-phenyl acetate followed by reduction with NaBH
4 and cleavage of hydroxyl protective group in acid condition, the corresponding optically active (+) Ⅳ and (-) Ⅳ were obtained. Compound (+) Ⅳ was treated with (+) dibenzoyltartaric acid and (-) Ⅳ by (-)dibenzoyltartaric acid, The epimeric salts were separated and purified by fractional crystallization from absolute alcohol. Four stereoisomers of anisodamine (6S, 2′S; 6S, 2′R; 6R, 2′R and 6R, 2′S) were thus obtained by neutralization of the corresponding salts.