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Structure and synthesis of phlobatannins related to the (4β,6:4α,8)-bis-fisetinidol-catechin profisetinidin triflavanoid

1996; Elsevier BV; Volume: 43; Issue: 1 Linguagem: Inglês

10.1016/0031-9422(96)00114-8

1873-3700

Susan L. Bonnet, Jan P. Steynberg, Barend C. B. Bezuidenhoudt, Catharina M. Saunders, Daneel Ferreira,

Bioactive natural compounds

Several members of the class of natural phlobatannins, representing the products of stereoselective pyran rearrangement of the 2,3-trans-3,4-trans- and 3,4-cis-flavan-3-ol units in the (4β,6:4α,8)-bis-fisetinidol-catechin triflavanoid have been characterized. These comprise a functionalized hexahydro-dipyrano-[2,3-f:2′,3′-h]-chromene, two fisetinidol-(4α,10)-tetrahydropyrano[2,3-f]chromenes and a pair of fisetinidol-(4α,10)-tetrahydropyrano[3,2-g]chromenes. The proposed structures of these novel compounds were confirmed by synthesis via base-catalysed conversion of the 4-O(E)-methyl ether of their presumed triflavanoid biogenetic precursor.