Structure and synthesis of phlobatannins related to bis-fisetinidol-epicatechin profisetinidin triflavanoids
1996; Elsevier BV; Volume: 43; Issue: 1 Linguagem: Inglês
10.1016/0031-9422(96)00240-3
ISSN1873-3700
AutoresSusan L. Bonnet, Jan P. Steynberg, Barend C. B. Bezuidenhoudt, Catharina M. Saunders, Daneel Ferreira,
Tópico(s)Multicomponent Synthesis of Heterocycles
ResumoThe class of natural phlobatannins originating by stereoselective pyran rearrangement of the 2,3-trans-3,4-trans- and 3,4-cis-flavan-3-ol moieties in the hitherto unknown bis-fisetinidol-(4,6:4,8)-epicatechin profisetinidins is extended by identification of several novel analogues. These comprise four functionalized hexahydrodipyrano[2,3-f:2′,3′-h]chromenes with an epicatechin DEF unit, as well as one based on an ent-catechin moiety, a fisetinidiol-(4α,10)-tetrahydropyrano[2,3-f]chromene and a fisetinidol-(4α,6)-tetrahydropyrano[2,3-h]chromene. The structure of one of the dipyranochromes was established unequivocally by synthesis via base-catalysed pyran ring rearrangement of the bis-fisetinidol-(4α,6:4α,8)-epicatechin triflavanoid.
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