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

被引：3

作者：

Shernyukov, A. V. ^{[1
]}

Mainagashev, I. Ya. ^{[1
]}

Korchagina, D. V. ^{[1
]}

Gatilov, Yu. V. ^{[1
]}

Salakhutdinov, N. F. ^{[1
]}

Tolstikov, G. A. ^{[1
]}

机构：

[1] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2011年 / 47卷 / 02期

关键词：

2,3-seco-28-oxo-19 beta,28-epoxy-18 alpha-olean-2,3-dicarboxylic acid; 2,3-secotriterpenoids; polyhydroxytriterpenoids; reduction; epsilon-lactone; oxepanes; BETULINIC ACID; DERIVATIVES; TRITERPENOIDS; LACTONE; NABH4; RING;

D O I：

10.1007/s10600-011-9891-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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.

引用

页码：237 / 242

页数：6

共 20 条

[1] NATURALLY-OCCURRING SECO-RING-A-TRITERPENOIDS AND THEIR POSSIBLE BIOLOGICAL SIGNIFICANCE [J].