POTENTIAL ROUTES TO FLAVAN-3-OLS .2. THE MITSUNOBU REACTIONS OF PARA-OXYGENATED BENZYLIC ALCOHOLS

被引:11
作者
BROWN, RFC [1 ]
JACKSON, WR [1 ]
MCCARTHY, TD [1 ]
机构
[1] MONASH UNIV,DEPT CHEM,CLAYTON,VIC 3168,AUSTRALIA
关键词
D O I
10.1016/S0040-4020(01)80702-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under mitsunobu reaction conditions para-methoxy benzylic alcohols give substantially racemic products, whereas para-pivaloyloxy and para-acetoxy benzylic alcohols give products resulting from inversion.
引用
收藏
页码:5469 / 5488
页数:20
相关论文
共 42 条
[1]  
AUGUSTYN JAN, 1990, TETRAHEDRON, V46, P2651
[2]   EFFECT OF STRUCTURE ON RATES OF SOME ALPHA-CHYMOTRYPSIN-CATALYZED REACTIONS [J].
BENDER, ML ;
NAKAMURA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (13) :2577-&
[3]  
BERTELLI A, 1974, NEW TRENDS THERAPY L, P92
[4]   REACTIONS OF METHYL THREO-2-ACETOXY-3-CHLORO-3-(4-METHOXYPHENYL)PROPANOATE AND METHYL CIS-2,3-EPOXY-3-(4-METHOXYPHENYL)PROPANOATE WITH 3,5-DIMETHOXYPHENOL - POTENTIAL ROUTES TO FLAVAN-3-OLS [J].
BROWN, RFC ;
JACKSON, WR ;
MCCARTHY, TD ;
FALLON, GD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1992, 45 (11) :1833-1843
[5]  
BROWN RFC, 1993, TETRAHEDRON LETT, P1195
[6]  
BUDAVARI S, 1989, MERCK INDEX ENCY CHE, P1074
[7]   ANTIHYPERLIPIDEMIC EFFECT OF FLAVONOIDS FROM PRUNUS-DAVIDIANA [J].
CHOI, JS ;
YOKOZAWA, T ;
OURA, H .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (01) :218-224
[8]   DNA STRAND SCISSION BY (-)-EPICATECHIN AND PROCYANIDIN-B2 [J].
CHRISEY, LA ;
BONJAR, GHS ;
HECHT, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :644-646
[9]  
COLVIN EW, 1988, SILICON REAGENTS ORG, pCH4
[10]   TRANS-BETA-TRIMETHYLSILYLVINYLLITHIUM [J].
CUNICO, RF ;
CLAYTON, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1480-1482