Abstract
The tropane alkaloids are divided into two major groups, those found in certain genera of the Solanaceae and those found in Erythroxylum spp. The solanaceous group includes species of Atropa (esp. A. belladonna), Datura, Duboisia, Hyoscyamus, Mandragora, and Scopolia. The best-known alkaloids of this group are (—)-hyoscyamine (1) and (—)-scopolamine (2) (hyoscine). (—)-Hyoscyamine and (—)-scopolamine are esters of tropic acid with the bases tropine and scopoline, respectively. Optical activity is contributed solely by the tropic acid residue since the bases have a plane of symmetry passing through C-3, the nitrogen atom, and the methyl group. In the accompanying conformational structures the C-3 ester group is shown as trans to the nitrogen atom, since it has this configuration in the best-known solanaceous tropane alkaloids. However, compounds with the opposite configuration are known both as synthetic derivatives and as naturally occurring alkaloids. They are designated by the prefix pseudo-. During pharmaceutical preparation of the esters of tropic acid, racemization readily occurs since the asymmetric carbon atom is adjacent to a carbonyl group and can enolize. DL-hyoscyamine resulting from this racemization is known as atropine.
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