Partial synthesis of chaksine

Abstract

This thesis is concerned with the preliminary studies in the synthesis of a monoterpenoid alkaloid, chaksine, Ethyl 2-methylcyclohexanone-6-carboxylate (XI) was hydroxymethylated with formaldehyde to give Ethyl 2-methyl~6-hydroxymethylcyclohexanone--6-Carboxylate (XII). Tosylation and cleavage of this product gave 2-methyl-6- carbethoxy-B-heptenoic (XIV) acid along with the diethyl ester (XIVa)» Ozonolysis of the diethyl ester yielded diethyl 2-keto-6-methyl pimelate (XV). A Wittig reaction v/ith diethyl cyanomethyl phosphonate (XVI) gave l-cyano-6~methyll- cyano-2, 6-dicarbethoxy-l-heptene (XVII). Other related studies involved: 1) Preparation of ethyl 2-methyl-6-vinylcyclohexanone-6-carboxylate (XXII), 2) A new method for preparation of 2-imidazolidones (XXIV). 3) Preparation of l-phenyl~2-aldehydo-6-methyl~l, 6-heptadiene (XXXIII) and l-n-butylthio-2-aldehydo-6-methyl-l, 6-heptadiene (XXXIX).