The formation and stability of flavans with 2,3-cis-3,4-cis configuration

被引：12
|
作者：
Coetzee, J
Malan, E
Ferreira, D
机构：
[1] Univ Orange Free State, Dept Chem, ZA-9300 Bloemfontein, South Africa
[2] Univ Mississippi, Sch Pharm, Pharmaceut Sci Res Inst, Natl Ctr Nat Prod Res, University, MS 38677 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 33期
关键词：
flavanoids; stereoselection; neighbouring group effects; thioethers;
D O I：
10.1016/S0040-4020(99)00558-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of 4 beta-chloroepioritin tri-O-methylether with phenylmethanethiol under neutral conditions affords both the 4 alpha- and 4 beta-substituted epioritin derivatives. The stereochemical course of the reaction is of relevance to the thiolysis of 5-oxy (A-ring) proanthocyanidins and to the conspicuous stability of the 7, 8-dihydroxy-2,3-cis-3,4-cis-flavan-3,4-diols, teracacidin and melacacidin, and of some of their all-cis (C-ring) oligomers. (C) 1999 Elsevier Science Ltd. Atl rights reserved.
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页码：9999 / 10004
页数：6
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