Structure and stereochemistry of triflavanoids containing both ether and carbon-carbon interflavanyl bonds. |
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| Authors: | L Bennie J Coetzee E Malan D Ferreira |
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| Institution: | Department of Chemistry, University of the Orange Free State, PO Box 339, 9300, Bloemfontein, South Africa. |
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| Abstract: | The first triflavanoids with both C-C and C-O-C interflavanyl bonds, epioritin-(4beta-->6)-epioritin-(4alpha-->4)-epioritin-4beta-ol, epioritin-(4beta-->3)-epioritin-(4beta-->6)-epioritin-4beta-ol and epioritin-(4beta-->3)-epioritin-(4beta-->6)-epimesquitol-4alpha-ol, were identified in the heartwood of Acacia caffra. The ethereal interflavanyl bond is readily susceptible to reductive cleavage with sodium cyanoborohydride in trifluoroacetic acid/dichloromethane which hence permits the unequivocal assignment of the absolute configuration of constituent flavanyl units. |
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