Abstract: Methods were proposed for preparing 15,16-dihydroisopimaric acid and its methyl ester. Oxidation of methyl dihydroisopimarate through the action of 3-chloroperbenzoic acid occurred with formation of 7,8-epoxy-derivatives and 7 alpha-hydroxydihydrosandaracopimarate. The latter in addition to 7-oxotetrahydroisopimarate were formed through the action of t-butylhydroperoxide in the presence of MoCl5. Oxidation of dihydroisopimaric acid or the ester by selenium dioxide in dioxane gave the corresponding 14 alpha-hydroxy-derivatives. Pyridinium chlorochromate transformed 14 alpha-hydroxydihydroisopimarate into a mixture of methyl esters of 7 alpha-hydroxy-8,14-epoxyisopimaric, 7-oxo-8,14-epoxyisopimaric, 7-oxo-14-hydroxyisopimaric, and 7 alpha-hydroxysandaracopimaric acids. Oximation of methyl 7-oxotetrahydroisopimarate by hydroxylamine hydrochloride in MeOH in the presence of NaOAc gave a mixture of the corresponding (Z)- and (E)-oximes. Beckmann rearrangement of the 7-(E)-oxime of methyl tetrahydroisopimarate through the action of thionylchloride led to tetradecahydrodibenzo[b,d]azepine.

Cite: Kharitonov Y.V. , Shul'ts E.E. , Shakirov M.M.
Synthetic Transformations of Higher Terpenoids. XXXIII. Preparation of 15,16-Dihydroisopimaric Acid and Methyl Dihydroisopimarate and their Transformations
Chemistry of Natural Compounds. 2014. V.49. N6. P.1067-1075. DOI: 10.1007/s10600-014-0823-1 WOS Scopus РИНЦ

Dates:

Published print:	Jan 1, 2014
Published online:	Jan 12, 2014

Identifiers:

Web of science	WOS:000330713200018
Scopus	2-s2.0-84894061142
Elibrary	21865679
OpenAlex	W2012617031

Altmetrics: