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.
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页码：3865 / 3868
页数：4
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