Studies on terpenoids from tecoma stans and eperua falcata

Part I Summary The chemistry and biosynthesis of cyclopentanoid monoterpene alkaloids is reviewed. The isolation of pyrindane and perhydropyrindane alkaloids from several samples of Teooma stans (Juss) and their separation by column and preparative vapour-phase chromatography is described. Four new alkaloids are characterised, two known alkaloids (tecomanine, boschniakine) are found and tentative structures are suggested for two more new alkaloids. A new attempted synthesis of the pyrindane ring system (1), which is unsuccessful, is described. This involves a Diels-Alder reaction between an oxazole and a cyclopentanoid dienophile, cyclopentene-3:5-dione and both chemical and photochemical methods are used. Part II Summary Part II of the thesis describes work carried out on products isolated from the exudate and wood of the Wallaba tree, Eperua falaata. The acid component of the exudate is shown to be eperuic acid. The neutral component is separated by chromatography on an alumina column and the benzene fraction is shown to contain a mixture of involatile esters, the main component of which is thought to be eperuyl eperuate. Separation of the methyl esters of the mixed acids from the branchwood is attempted by both preparative-layer and column chromatography but is unsuccessful