Tetrahedron p. 7859 - 7868 (1989)
Update date:2022-08-03
Topics:
Malan, Johannes C. S.
Steenkamp, Jacobus A.
Young, Desmond A.
Ferreira, Daneel
Acid-catalyzed condensation of (+)-mollisacacidin<(2R,3S,4R)-2,3-trans-3,4-trans-flavan-3,3',4,4',7-pentaol> with an excess of (-)-robinetinidol<(2R,3S)-2,3-trans-flavan-3,3',4,4',5',7-pentaol> afforded a novel series of bi-, tri-, and tetraflavanoid profisetinidins.They are accompanied by (-)-fisetinidol-(4α,2')-(-)-robinetinidol which results from the pyrogallol B-ring of (-)-robinetinidol serving as nucleophile competing with its resorcinol A-ring in coupling with a C-4 carbocationic intermediate.Similar condensation with (+)-epifisetinidol<(2S,3S)-2,3-cis-flavan-3,3',4',7-tetraol> led to the exclusive formation of <4,6>-interflavanyl bonds, these units being 'linearly' arranged in the tetraflavanoid analogue in contrast to the 'branched' nature of the (-)-robinetinidol homologue.
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