Structure and stereochemistry of triflavanoids containing both ether and carbon - Carbon interflavanyl bonds

Phytochemistry

Volumn 57, Issue 6, 2001, Pages 1023-1034

  Bennie, Linette ^a   Coetzee, Johan ^a   Malan, Elfranco ^a   Ferreira, Daneel ^b  

^a UNIVERSITY OF THE FREE STATE   (South Africa)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Absolute configuration; Acacia caffra; Leguminosae; Pro leucoanthocyanidins; Pro leucomelacacinidins; Pro leucoteracacinidins; Reductive cleavage; Triflavanoids

Indexed keywords

BIOFLAVONOID; CARBON; DICHLOROMETHANE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ETHER DERIVATIVE; FLAVANOID; PHENOL DERIVATIVE; SODIUM BOROHYDRIDE; SOLVENT; TRIFLUOROACETIC ACID; WOOD;

ACACIA; ANGIOSPERM; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ETHERS; FLAVONOIDS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENOLS; ROSALES; SOLVENTS; WOOD;

ACACIA; ACACIA CAFFRA; FABACEAE;

EID: 0035800164     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(01)00044-9     Document Type: Article

References (25)

1. Enantioselective synthesis of flavonoids. Part 2. Poly-oxygenated α-hydroxydihydrochalcones and circular dichroic assessment of their absolute configuration
2. Plant proanthocyanidins. Part 6. Chiroptical studies. Part 94. Circular dichroism of procyanidins
3. Structure and synthesis of ether-linked proteracacinidin and promelacacinidin proanthocyanidins from Acacia caffra
4. Synthesis of condensed tannins. Part 4. A direct biomimetic approach to [4,6]- and [4,8]-biflavanoids
5. Flavan derivatives. Part XVII. Epimerization of the benzylic 4-hydroxyl group in flavan-3,4-diols and the formation of 4-alkyl ethers by solvolysis
6. Oligomeric flavanoids. Part 28, Structure and synthesis of ether-linked (4-O-3)-bis-teracacinidins, a novel class of naturally occurring proanthocyanidins
7. Oligomeric flavanoids. Part 29. Structure and synthesis of novel ether-linked [4-O-4] bisteracacinidins
8. The formation and stability of flavans with 2,3-cis-3,4-cis configuration
9. Synthesis and reactions of flav-3-en-3-ols
10. Circular dichroism studies-I. A quadrant rule for the optically active aromatic chromophore in rigid polycyclic systems
11. Oligomeric proanthocyanidins. Naturally occurring O-heterocycles
12. Oligomeric proanthocyanidins-naturally occurring O-heterocycles
13. Isolation of [4-0-4]-linked biflavanoids from Acacia melanoxylon: First examples of a new class of single ether-linked proanthocyanidin dimers
14. Circular dichroism spectra of flavanols
15. A-type proanthocyanidins from peanut skins
16. The structure and synthesis of the first dimeric proteracacinidins from Acacia galpinii
17. Conformational analysis of oligomeric flavanoids. Part 1. 4-Arylflavan-3-ols
18. Cleavage of the acetal functionality in A-type proanthocyanidins
19. Oligomeric flavanoids. Part 19. Reductive cleavage of the interflavanyl bond in proanthocyanidins
20. Synthesis of condensed tannins. Part 2. Synthesis by photolytic rearrangement, stereochemistry, and circular dichroism of the first 2,3-cis-3,4-cis-4-arylflavan-3-ols
21. Circular dichroic properties of flaven-3-ols