Absolute configuration of (-)anisodine (a new ganglio blocking agent) and (-)anisodinic acid.

Abstract

A new tropane alkaloid, (-)anisodine (I), was isolated from the plant of Anisodus tanguticus. It is a novel ganglio blocking agent. The absolute configuration of (-)anisodinic acid (VII), which is the side chain of (-)anisodine, was determined by chemical correlation with (R) (-)-2-phenyl-1, 2-propanediol (IV) and (R) (-)-2-hydroxy-2-phenylpropionic acid (VI). Thereby (-)anisodine with the absolute configuration shown as (I) is 6 beta, 7 beta-epoxy-1 alpha H, 5 alpha H-tropan-3 alpha-ol (S) 2'-phenyl-2', 3'-dihydroxypropionate. Two new tropane alkaloids; 6 beta, 7 beta-epoxy-1 alpha H, 5 alpha H-tropan-3 alpha-ol 2',3'-epoxypropionate (III) and 2'-phenyl-2'-hydroxypropionate (V) were prepared and its physical constant is reported in this paper.