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).
collections
- retrospective theses [1604]