Conformational analysis of oligomeric flavanoids. 2—methyl ether acetate derivatives of profisetinidins

✍ Scribed by Jan P. Steynberg; E. Vincent Brandt; Daneel Ferreira; Carin A. Helfer; Wayne L. Mattice; Dominika Gornik; Richard W. Hemingway

• Book ID: 102952475
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 853 KB
• Volume: 33
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260330802

✦ Synopsis

Abstract

The profisetinidins are the most important polyflavanoids of commerce, making up the major constituents of wattle and quebracho tannins. Even within the dimeric profisetinidins, substantial complexity exists because of stereo‐, regio‐, rotational and conformational isomers. Definition of the stereochemistry of the upper and lower flavan units, the location of the interflavanoid bond, the conformation of the heterocyclic rings in the upper and lower flavan units and the conformations of major and minor rotational isomers in a series of methyl ether acetate derivatives of dimeric profisetinidin diastereomers is possible by application of COSY and NOE experiments. All compounds studied were present in two rotameric forms with the more compact conformation favored. The heterocyclic ring in the upper chain extender unit was predominantly in an E‐conformation (i.e. half‐chair in 2__R__,3__S__ isomers and a ‘reverse’ half‐chair in the 2__S__,3__R__ isomers). The heterocyclic ring conformation of the terminal cate‐chin unit, although mostly in an E‐conformation, was often represented by significant proportions of A‐conformers.