Tropane and Related Alkaloids

Abstract

Tropane alkaloids comprise a large group of bases occurring predominantly in the family of the Solanaceae. Structurally they are esters of carboxylic acids with tropine (3-hydroxy-8-aza-8-methyl-[3.2.1]-bicyclooctane) and are biosynthetically derived from amino acid and acetate precursors. Despite the relative structural simplicity of the alkaloids, their biosynthesis is not well understood from a mechanistic point of view. In this article the available information pertaining to this question is summarized and discussed in context with the information that is available from the analogous pelletierine class of alkaloids. A new proposal for the mechanism of assembly of the acetate derived C3 fragment of these alkaloids is introduced.