Oligomeric flavanoids. Part 26. Structure and synthesis of the first profisetinidins with epifisetinidol constituent units

Abstract

The natural occurrence of the first oligomeric profisetinidins with (2R,3R)-2,3-cis-epifisetinidol chain extender units is demonstrated in the bark of Pithecellobium dulce (Guamúchil). Semi-synthesis using the appropriate flavan-3-ol and flavan-3,4-diol precursors permits unequivocal structural and stereochemical assignment of the novel dimeric epifisetinidol-(4β,8)-catechin and epicatechins 16 and 18, the trimeric bis-epifisetinidol-(4β,6:4β ,8)-catechin and epicatechins 33 and 35, the fisetinidol-(4α,8)-catechin-(6,4β)- epifisetinidol 37 and fisetinidol-(4α,8)-epicatechin-(6,4β)- epifisetinidol 39.