Enantioselective synthesis of (2R,3S)-(+)-catechin

被引：29

作者：

Jew, S

Lim, D

Bae, S

Kim, H

Kim, J

Lee, J

Park, H ^{[1
]}

机构：

[1] Seoul Natl Univ, Pharmaceut Sci Res Inst, Seoul 151742, South Korea

[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(02)00182-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new enantioselective synthetic method for catechin from trans-methyl cinnamate derivative was developed via asymmetric dihydroxylation (ADH), the addition of an aryllithium species, followed by the Barton-McCombie reaction and all intramolecular Mitsunobu reaction as key steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：715 / 720

页数：6

相关论文

共 21 条

[1] PHOTOLYTIC GENERATION OF CARBON RADICALS FROM BARTON ESTERS - RECENT DEVELOPMENTS [J].

BARTON, DHR ;

JASZBERENYI, JC ;

TANG, DG .

TETRAHEDRON LETTERS, 1993, 34 (21) :3381-3384

[2] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[3]

BOHM BA, 1994, FLAVANOIDS ADV RES 1, P23

[4]

BROWN BR, 1986, J CHEM RES-S, P140

[5]

CAO Y, 1999, NATURE, V38, P398

[6]

Choi J S, 1994, Arch Pharm Res, V17, P71, DOI 10.1007/BF02974226

[7] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[8] Tumor invasion: molecular shears blunted by green tea [J].

Garbisa, S ;

Biggin, S ;

Cavallarin, N ;

Sartor, L ;

Benelli, R ;

Albini, A .

NATURE MEDICINE, 1999, 5 (11) :1216-1216

[9] Enantioselective synthetic method for 3-hydroxyflavanones:: an approach to (2R,3R)-3′,4′-O-dimethyltaxifolin [J].

Jew, S ;

Kim, H ;

Bae, S ;

Kim, J ;

Park, H .

TETRAHEDRON LETTERS, 2000, 41 (41) :7925-7928

[10] FLAVONOIDS AS ANTIOXIDANTS [J].

JOVANOVIC, SV ;

STEENKEN, S ;

TOSIC, M ;

MARJANOVIC, B ;

SIMIC, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4846-4851