STEREOCHEMISTRY AND DYNAMIC BEHAVIOR OF SOME SYNTHETIC ANGULAR PROFISETINIDIN TETRAFLAVANOID DERIVATIVES

被引:9
作者
YOUNG, DA [1 ]
FERREIRA, D [1 ]
ROUX, DG [1 ]
机构
[1] UNIV ORANGE FREE STATE,DEPT CHEM,POB 339,BLOEMFONTEIN 9300,SOUTH AFRICA
关键词
ORGANIC COMPOUNDS - Synthesis;
D O I
10.1002/pola.1986.080240503
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The structure and stereochemistry of four synthetic 'angular' tetraflavanoid-condensed tannin derivatives are examined by high-resolution variable temperature **1H NMR spectroscopy, and hence correlated with their dynamic behavior. Three 'angular' oligomers exist as stable rotational isomers at ambient temperatures, thus contrasting with the mobility about their interflavanoid bonds of most natural profisetinidin 'trimeric' and 'tetrameric' homologs. A 'linear' tetraflavanoid analog results from one of these regioselectively controlled condensations.
引用
收藏
页码:835 / 849
页数:15
相关论文
共 12 条
[1]   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
[2]   SYNTHESIS OF CONDENSED TANNINS .5. THE 1ST ANGULAR [4,6-4,8]-TRIFLAVANOIDS AND THEIR NATURAL COUNTERPARTS [J].
BOTHA, JJ ;
VIVIERS, PM ;
YOUNG, DA ;
DUPREEZ, IC ;
FERREIRA, D ;
ROUX, DG ;
HULL, WE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :527-533
[3]  
DUPREEZ IC, 1971, J CHEM SOC CHEM COMM, P333
[4]   STRUCTURAL CONSIDERATIONS IN PREDICTING THE UTILIZATION OF TANNINS [J].
ROUX, DG ;
FERREIRA, D ;
BOTHA, JJ .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1980, 28 (02) :216-222
[5]   SYNTHESIS OF CONDENSED TANNINS .2. SYNTHESIS BY PHOTOLYTIC REARRANGEMENT, STEREOCHEMISTRY, AND CIRCULAR-DICHROISM OF THE 1ST 2,3-CIS-3,4-CIS-4-ARYLFLAVAN-3-OLS [J].
VANDERWESTHUIZEN, JH ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1220-1226
[6]   SYNTHESIS OF CONDENSED TANNINS .11. INTRAMOLECULAR ENANTIOMERISM OF THE CONSTITUENT UNITS OF TANNINS FROM THE ANACARDIACEAE - STOICHIOMETRIC CONTROL IN DIRECT SYNTHESIS - DERIVATION OF H-1 NUCLEAR MAGNETIC-RESONANCE PARAMETERS APPLICABLE TO HIGHER OLIGOMERS [J].
VIVIERS, PM ;
KOLODZIEJ, H ;
YOUNG, DA ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2555-2562
[7]   SYNTHESIS OF CONDENSED TANNINS .7. ANGULAR [4,6-4,8]-PROROBINETINIDIN TRIFLAVANOIDS FROM BLACK WATTLE (MIMOSA) BARK EXTRACT [J].
VIVIERS, PM ;
BOTHA, JJ ;
FERREIRA, D ;
ROUX, DG ;
SAAYMAN, HM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (01) :17-22
[8]   SYNTHESIS OF CONDENSED TANNINS .6. THE SEQUENCE OF UNITS, COUPLING POSITIONS AND ABSOLUTE-CONFIGURATION OF THE 1ST LINEAR [4,6-4,6]-TRIFLAVANOID WITH TERMINAL 3,4-DIOL FUNCTION [J].
VIVIERS, PM ;
YOUNG, DA ;
BOTHA, JJ ;
FERREIRA, D ;
ROUX, DG ;
HULL, WE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :535-540
[9]  
YOUNG DA, UNPUB
[10]  
YOUNG DA, 1986, UNPUB J CHEM S P1 16