REDUCTION OF 2,3-Seco-28-OXO-19 beta,28-EPOXY-18 alpha-OLEAN-2,3-DICARBOXYLIC ACID AND ITS CYCLIC ANHYDRIDE

REDUCTION OF 2,3-Seco-28-OXO-19 beta,28-EPOXY-18 alpha-OLEAN-2,3-DICARBOXYLIC ACID AND ITS CYCLIC ANHYDRIDE Full article

Journal

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

Output data

Year: 2011, Volume: 47, Number: 2, Pages: 237-242 Pages count : DOI: 10.1007/s10600-011-9891-7

Tags

2,3-seco-28-oxo-19 beta,28-epoxy-18 alpha-olean-2,3-dicarboxylic acid; 2,3-secotriterpenoids; polyhydroxytriterpenoids; reduction; epsilon-lactone; oxepanes

Authors

Shernyukov A. V. ¹ , Mainagashev I. Ya. ¹ , Korchagina D. V. ¹ , Gatilov Yu. V. ¹ , Salakhutdinov N. F. ¹ , Tolstikov G. A. ¹

Affiliations

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

Reduced derivatives of 2,3-seco-28-oxo-19 beta,28-epoxy-18 alpha-olean-2,3-dicarboxylic acid and its cyclic anhydride were prepared. Reduction of the starting 2,3-secodicarboxylic acid by NaBH(4)-I(2) produced the 2,3-seco-2,3-dihydroxy derivative. Reaction of the starting anhydride with LiAlH(4) gave the 2,3-seco-2,3,19 beta,28-tetrahydroxy derivative. Cyclization using acidic reagents of the 2,3-seco-2,3-hydroxy- and 2,3-seco-2,3,19 beta,28-tetrahydroxy derivatives gave the corresponding cyclic ethers containing an oxepane ring. The anhydride ring was reduced by NaBH(4) to the corresponding epsilon-lactone, the structure of which was confirmed by an x-ray crystal structure.

Shernyukov A.V. , Mainagashev I.Y. , Korchagina D.V. , Gatilov Y.V. , Salakhutdinov N.F. , Tolstikov G.A.
REDUCTION OF 2,3-Seco-28-OXO-19 beta,28-EPOXY-18 alpha-OLEAN-2,3-DICARBOXYLIC ACID AND ITS CYCLIC ANHYDRIDE
Chemistry of Natural Compounds. 2011. V.47. N2. P.237-242. DOI: 10.1007/s10600-011-9891-7 WOS Scopus РИНЦ

Published print:	May 1, 2011
Published online:	Jun 7, 2011

Web of science	WOS:000292637100020
Scopus	2-s2.0-79959772781
Elibrary	16996085
OpenAlex	W2014987178