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

✍ Scribed by Johan Coetzee; Elfranco Malan; Daneel Ferreira

• Book ID: 104209541
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 292 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00558-x

✦ Synopsis

Treatment of 4J$-chloroepioritin tri-O-methylether with phenylmethanethiol under neutral conditions affords both the 4a-and 4[~-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-dlhydroxy-2,3-c/s-3,4-c/s-flavan-3,4-diols, teracacidin end melacacidin, and of some of their all-c/s (C-ring) oligomers.