Oligomeric flavanoids - Part 29: Structure and synthesis of novel ether-linked [4-O-4]bis-teracacinidins

被引:15
作者
Coetzee, J [1 ]
Malan, E [1 ]
Ferreira, D [1 ]
机构
[1] Univ Orange Free State, Dept Chem, ZA-9300 Bloemfontein, South Africa
关键词
D O I
10.1016/S0040-4020(98)00552-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rare series of proteracacinidin-type oligoflavanoids is extended by identification of two novel [4-O-4] ether-linked analogues 7 and 10 from the heartwood of Acacia galpinii. Their structures and absolute configuration were established via spectroscopic methods and by stereoselective synthesis from the appropriate leucoteracacinidin flavan-3,4-diol precursors. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9153 / 9160
页数:8
相关论文
共 18 条
[1]   PLANT PROANTHOCYANIDINS .6. CHIROPTICAL STUDIES .95. CIRCULAR-DICHROISM OF PROCYANIDINS [J].
BARRETT, MW ;
KLYNE, W ;
SCOPES, PM ;
FLETCHER, AC ;
PORTER, LJ ;
HASLAM, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (10) :2375-2377
[2]   SYNTHESIS OF CONDENSED TANNINS .4. A DIRECT BIOMIMETIC APPROACH TO [4,6]-BIFLAVANOIDS AND [4,8]-BIFLAVANOIDS [J].
BOTHA, JJ ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1235-1245
[3]   CONDENSED TANNINS - DIRECT SYNTHESIS, STRUCTURE, AND ABSOLUTE-CONFIGURATION OF 4 BIFLAVANOIDS FROM BLACK WATTLE BARK (MIMOSA) EXTRACT [J].
BOTHA, JJ ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :700-702
[4]   CONDENSED TANNINS - CIRCULAR-DICHROISM METHOD OF ASSESSING ABSOLUTE-CONFIGURATION AT C-4 OF 4-ARYLFLAVAN-3-OLS, AND STEREOCHEMISTRY OF THEIR FORMATION FROM FLAVAN-3,4-DIOLS [J].
BOTHA, JJ ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :698-700
[5]   SYNTHESIS OF CONDENSED TANNINS .1. STEREOSELECTIVE AND STEREOSPECIFIC SYNTHESES OF OPTICALLY PURE 4-ARYLFLAVAN-3-OLS, AND ASSESSMENT OF THEIR ABSOLUTE STEREOCHEMISTRY AT C-4 BY MEANS OF CIRCULAR-DICHROISM [J].
BOTHA, JJ ;
YOUNG, DA ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1213-1219
[6]  
CLARKLEWIS JW, 1967, AUST J CHEM, V20, P2151
[7]  
COETZEE J, 1998, IN PRESS J CHEM RES
[8]   CIRCULAR DICHROISM STUDIES .I. A QUADRANT RULE FOR OPTICALLY ACTIVE AROMATIC CHROMOPHORE IN RIGID POLYCYCLIC SYSTEMS [J].
DEANGELIS, GG ;
WILDMAN, WC .
TETRAHEDRON, 1969, 25 (20) :5099-+
[9]   DIOXAN-LINKED BIFLAVANOID FROM HEARTWOOD OF ACACIA MEARNSII [J].
DREWES, SE ;
ILSLEY, AH .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (06) :897-&
[10]   Oligomeric proanthocyanidins: Naturally occurring O-heterocycles [J].
Ferreira, D ;
Bekker, R .
NATURAL PRODUCT REPORTS, 1996, 13 (05) :411-433