127612-93-5Relevant articles and documents
Oligomeric Flavanoids. Part 8. The First Profisetinidins and Proguibourtinidins Based on C-8 Substituted (-)-Fisetinidol Units and Related c-ring Isomerized Analogues
Malan, Johannes C. S.,Steenkamp, Jacobus A.,Steynberg, Jan P.,Young, Desmond A.,Brandt, E. Vincent,Ferreira, Daneel
, p. 209 - 218 (2007/10/02)
Structural examination of the phenolic metabolites of Colophospermum mopane reveals the presence of the first profisetinidins and proguibourtinidins based on C-8 substituted (-)-fisetinidol units i.e. the (4α,8)-bis-(-)-fisetinidol (1), (+)-epifisetinidol-(4α,8)-(-)-fisetinidol (3), and the (+)-guibourtinidol-(4α,8)-(-)-fisetinidol (5).They are accompanied by the related functionalized tetrahydropyranochromenes (9), (11), (13), (15), and (17), and by a 2,4-diaryl-6-(2-benzopyranyl)chroman (19), the first C-ring isomerised analogue derived from a B-ring coupled profisetinidin.Efforts towards the synthesis of the (4,8)-bis-fisetinidols from 6-bromo-(-)-fisetinidol and the appropriate flavan-3,4-diol, lead to the biaryl type biflavanoids (33) and (35).Their genesis is explained in terms of an oxidative substitution reaction initiated by bromonium ion.