SYNTHETIC TRANSFORMATIONS OF HIGHER TERPENOIDS. XXXIV. PREPARATION OF CARBOXYL DERIVATIVES OF ISOPIMARIC ACID

SYNTHETIC TRANSFORMATIONS OF HIGHER TERPENOIDS. XXXIV. PREPARATION OF CARBOXYL DERIVATIVES OF ISOPIMARIC ACID Full article

Journal

Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388

Output data

Year: 2014, Volume: 50, Number: 4, Pages: 673-680 Pages count : DOI: 10.1007/s10600-014-1050-5

Tags

isopimaric acid; N-substituted amides; 2,5-disubstituted oxazoles; 5-methyleneoxazoles; cycloisomerization; bromination

Authors

Timoshenko M. A. ^1,2 , Ayusheev A. B. ^1,2 , Kharitonov Yu. V. ¹ , Shakirov M. M. ¹ , Shul'ts E. E. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

New isopimaric acid derivatives containing amines and methyl esters of alpha-, beta-, and omega-amino acids were prepared. Conditions were found for cyclic isomerisation of isopimaric acid propargylamide into 2-(dodecahydrophenanthren-1-yl)-5-methyloxazole or 2-(dodecahydrophenanthren-1-yl)-5-methylene-4,5-dihydrooxazole. The latter was selectively modified by adding the methyl ester of (2-methylamino) butanoic acid at the oxazole C-5 position.

Timoshenko M.A. , Ayusheev A.B. , Kharitonov Y.V. , Shakirov M.M. , Shul'ts E.E.
SYNTHETIC TRANSFORMATIONS OF HIGHER TERPENOIDS. XXXIV. PREPARATION OF CARBOXYL DERIVATIVES OF ISOPIMARIC ACID
Chemistry of Natural Compounds. 2014. V.50. N4. P.673-680. DOI: 10.1007/s10600-014-1050-5 WOS Scopus РИНЦ

Published online:	Sep 14, 2014
Published print:	Oct 1, 2014

Web of science	WOS:000343212900021
Scopus	2-s2.0-84911942405
Elibrary	24006961
OpenAlex	W2088918814