Procyanidin oligomers. A new method for 4→8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy

被引：14

作者：

Dennis, Eric G. ^{[1
,2
]}

Jeffery, David W. ^{[1
]}

Johnston, Martin R. ^{[2
]}

Perkins, Michael V. ^{[2
]}

Smith, Paul A. ^{[1
]}

机构：

[1] Australian Wine Res Inst, Glen Osmond, SA 5064, Australia

[2] Flinders Univ S Australia, Sch Chem & Phys Sci, Adelaide, SA 5001, Australia

来源：

TETRAHEDRON | 2012年 / 68卷 / 01期

关键词：

Iterative synthesis; Procyanidin oligomers; Lewis acid-promoted coupling; Benzyl ether; Procyanidin B3; Boron-protection; RADICAL-SCAVENGING ACTIVITY; CANCER-CELL GROWTH; STEREOSELECTIVE-SYNTHESIS; POLYPHENOL CHEMISTRY; INHIBITORY-ACTIVITY; PROANTHOCYANIDINS; CATECHIN; ANTIOXIDANT; DIMERS; CONDENSATION;

D O I：

10.1016/j.tet.2011.10.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Interest in the synthesis of procyanidin (catechin or epicatechin) oligomers that contain the 4 -> 8 interflavan linkage remains high, principally due to research into their health effects. A novel coupling utilising a C8-boronic acid as a directing group was developed in the synthesis of natural procyanidin 83 (i.e., 3,4-trans-(+)-catechin-4 alpha -> 8-(+)-catechin dimer). The key interflavan bond was forged using a novel Lewis acid-promoted coupling of C4-ether 6 with C8-boronic acid 16 to provide the a-linked dimer with high diastereoselectivity. Through the use of a boron protecting group, the new coupling procedure was extended to the synthesis of a protected procyanidin trimer analogous to natural procyanidin C2. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：340 / 348

页数：9

共 49 条

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

Achilonu, Matthew C. ;

Bonnet, Susan L. ;

van der Westhuizen, Jan H. .

ORGANIC LETTERS, 2008, 10 (17) :3865-3868

[2] Procyanidin B3 synthesis: a study of leaving group and Lewis acid activator effects upon interflavan bond formation [J].

Alharthy, Rima D. ;

Hayes, Christopher J. .

TETRAHEDRON LETTERS, 2010, 51 (08) :1193-1195

[3] Hypolipidemic effects of proanthocyanidins and their underlying biochemical and molecular mechanisms [J].

Blade, Cinta ;

Arola, Lluis ;

Salvado, Maria-Josepa .

MOLECULAR NUTRITION & FOOD RESEARCH, 2010, 54 (01) :37-59

[4] Suzuki cross-coupling reaction of sterically hindered aryl boronates with 3-iodo-4-methoxybenzoic acid methylester [J].

Chaumeil, H ;

Signorella, S ;

Le Drian, C .

TETRAHEDRON, 2000, 56 (49) :9655-9662

[5]

Cheynier V, 2005, AM J CLIN NUTR, V81, p223S, DOI 10.1093/ajcn/81.1.223S

[6]

Cheynier V, 2006, AM J ENOL VITICULT, V57, P298

[7] Biological evaluation of proanthocyanidin dimers and related polyphenols [J].

De Bruyne, T ;

Pieters, L ;

Witvrouw, M ;

De Clercq, E ;

Vanden Berghe, D ;

Vlietinck, AJ .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (07) :954-958

[8]

de Gaulejac NV, 2001, J INT SCI VIGNE VIN, V35, P51

[9] Pd(DPEPhos)Cl2-catalyzed Negishi cross-couplings for the formation of biaryl and diarylmethane phloroglucinol adducts [J].

Dennis, Eric G. ;

Jeffery, David W. ;

Perkins, Michael V. ;

Smith, Paul A. .

TETRAHEDRON, 2011, 67 (11) :2125-2131

[10] Proanthocyanidins - a final frontier in flavonoid research? [J].

Dixon, RA ;

Xie, DY ;

Sharma, SB .

NEW PHYTOLOGIST, 2005, 165 (01) :9-28

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