Synthetic studies on chaksine / by John Bruce Evans

Abstract

This thesis is concerned with the preliminary studies in the synthesis of a monoterpenoid alkaloid, chaksine. Diethyl methylmalonate was alkylated with 1,3-dibromo propane to give 2-(3-bromopropyl)-2-methylmalonate. Hydrolysis and decarboxylation of this product gave the mono acid which was then converted to the corresponding ethyl ester. Reduction with lithium borohydride yielded the primary alcohol to which a tetrahydropyran protective group was added. Alkylation with diethyl malonate followed by acylation with the mixed anhydride of isovaleric acid and carbobenzyloxyglycine gave diethyl (see document for formula).