Synthesis of proanthocyanidins. Part 1. The first oxidative formation of the interflavanyl bond in procyanidins

被引：21

作者：

Achilonu, Matthew C. ^{[1
]}

Bonnet, Susan L. ^{[1
]}

van der Westhuizen, Jan H. ^{[1
]}

机构：

[1] Univ Orange Free State, Dept Chem, ZA-9301 Bloemfontein, South Africa

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 17期

关键词：

D O I：

10.1021/ol801353u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient method for the oxidative condensation of tetra-O-methyl-3-oxocatech in 4 with tetra-O-methylcatechin is described. Treatment of a solution of 3 (2 equiv) and 4 (1 equiv) with silver tetrafluoroborate readily affords the phenolic per-O-methyl ethers of 3-oxocatechin(4-8)-catechin 18 and 19. Subsequent metal hydride reduction provides access to procyanidin B-3 analogues with the 3,4-cis diastereomers predominating.

引用

页码：3865 / 3868

页数：4

共 25 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] 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

[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] Dietary antioxidants and lung cancer risk: A case-control study in Uruguay [J].

De Stefani, E ;

Boffetta, P ;

Deneo-Pellegrini, H ;

Mendilaharsu, M ;

Carzoglio, JC ;

Ronco, A ;

Olivera, L .

NUTRITION AND CANCER-AN INTERNATIONAL JOURNAL, 1999, 34 (01) :100-110

[7] SYNTHESIS OF CONDENSED TANNINS .9. THE CONDENSATION SEQUENCE OF LEUCOCYANIDIN WITH (+)-CATECHIN AND WITH THE RESULTANT PROCYANIDINS [J].

DELCOUR, JA ;

FERREIRA, D ;

ROUX, DG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1711-1717

[8]

GEISSMAN TA, 1966, TETRAHEDRON LETT, P2669

[9]

Hegarty VM, 2000, AM J CLIN NUTR, V71, P1003

[10]

HERTOG MG, 1995, ARCH INTERN MED, V155

← 1 2 3 →