REDUCTION OF 2,3-Seco-28-OXO-19 beta,28-EPOXY-18 alpha-OLEAN-2,3-DICARBOXYLIC ACID AND ITS CYCLIC ANHYDRIDE Full article
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Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388 |
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| 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 | ||
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Abstract:
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.
Cite:
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 OpenAlex
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 OpenAlex
Dates:
| Published print: | May 1, 2011 |
| Published online: | Jun 7, 2011 |
Identifiers:
| Web of science: | WOS:000292637100020 |
| Scopus: | 2-s2.0-79959772781 |
| Elibrary: | 16996085 |
| OpenAlex: | W2014987178 |