HETEROCYCLES .25. SODIUM-BOROHYDRIDE REDUCTION OF FLAVANONES

被引：6

作者：

LI, SS ^{[1
]}

ONDA, MU ^{[1
]}

KAGAWA, H ^{[1
]}

KAWASE, H ^{[1
]}

IGUCHI, M ^{[1
]}

HARIGAYA, Y ^{[1
]}

机构：

[1] KITASATO UNIV,SCH PHARMACEUT SCI,MINATO KU,TOKYO 108,JAPAN

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1990年 / 27卷 / 07期

关键词：

D O I：

10.1002/jhet.5570270734

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solvent effects on the stereochemistry in the sodium borohydride reduction of (+/-)-flavanonols have been examined. The effects observed for the (+/-)-flavanonols with 5-OMe in 2-propanol, dioxane and methanol are explainable by the differences between the steric interactions inherent in the product-like transition states A and B. It has been also found that 5-OAc peculiarly affects the stereochemistry in the reduction to produce the (+/-)-catechin-type compounds in a one-pot process. The solvent and temperature effects are examined using a model analogous to the above.

引用

页码：2029 / 2035

页数：7

共 16 条

[1] INFLUENCE OF SOLVENT AND METAL ION ON RATE OF REACTION OF ALKALI METAL BOROHYDRIDES WITH ACETONE [J].

BROWN, HC ;

ICHIKAWA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (21) :4372-&

[2] KINETICS OF REDUCTION OF ACETOPHENONES BY ALKALI-METAL ALKOXIDES, AND MECHANISM OF REDUCTION OF KETONES BY BOROHYDRIDE [J].

BURNETT, RD ;

KIRK, DN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (13) :1523-1526

[3]

CARO B, 1974, TETRAHEDRON LETT, P3539

[4]

CARO B, 1974, TETRAHEDRON LETT, P2061

[5] A NEW FLAVAN-3,4-DIOL FROM ACACIA AURICULIFORMIS BY PAPER IONOPHORESIS [J].

DREWES, SE ;

ROUX, DG .

BIOCHEMICAL JOURNAL, 1966, 98 (02) :493-&

[6] REDUCTION WITH METAL HYDRIDES .19. COMPETITIVE REDUCTION OF ALKYLCYCLOHEXANONES - REGARDING CONCEPTS OF STERIC APPROACH CONTROL AND PRODUCT DEVELOPMENT CONTROL [J].

ELIEL, EL ;

SENDA, Y .

TETRAHEDRON, 1970, 26 (10) :2411-&

[7] HETEROCYCLES .24. SYNTHESIS OF OPTICALLY PURE 2,3-TRANS-5,7,3',4',5'-PENTAHYDROXYFLAVAN-3,4-DIOLS AND COMPARISON WITH NATURALLY-OCCURRING LEUCODELPHINIDINS [J].

ONDA, M ;

LI, SS ;

LI, XA ;

HARIGAYA, Y ;

TAKAHASHI, H ;

KAWASE, H ;

KAGAWA, H .

JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05) :1100-1106

[8] A NEW SYNTHESIS OF POLYHYDROXYDIHYDROFLAVONOLS [J].

OYAMADA, T ;

BABA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1966, 39 (03) :507-+

[9] CONFIGURATION OF GUIBOURTACACIDIN AND SYNTHESIS OF ISOMERIC RACEMATES [J].

SAAYMAN, HM ;

ROUX, DG .

BIOCHEMICAL JOURNAL, 1965, 96 (01) :36-&

[10]

TAKAHASHI H, 1987, HETEROCYCLES, V26, P3239

← 1 2 →