Synthetic studies in the Galbulimima series of alkaloids.

Abstract

The thesis is divided into two sections, the first of which describes the synthesis of methylene cyclohexane. The simplest and most efficient method was found to be by decarboxylation and dehydration of l-hydroxy cyclohexylecetic acid. The second section includes a description of the conversion of this olefine to cyclohexenylmethyl succinic anhydride (2) by w Diels-Alder type addition of meleic enhydride and consequent intramolecular acylation of the adduct to yield the unsaturated L-decalone-a-cerboxylic acid (3). The structure of this last compound has been established conclusively and several routes for introducing a nitrogen atom into the molecule have been explored. In this way it has been possible to synthesise simple analogues of the alkaloids of the Galbulimina species.