Heterocycles p. 1595 - 1602 (2014)
Update date:2022-08-03
Topics:
Ishihara, Sayaka
Doi, Syoma
Harui, Kota
Okamoto, Taisuke
Okamoto, Shuhei
Uenishi, Joji
Kawasaki, Takashi
Nakajima, Noriyuki
Saito, Akiko
Proanthocyanidins, also known as condensed tannins and/or oligomeric flavonoids, are found in many edible plants and show interesting various biological activities. We report a simple new proanthocyanidin synthesis strategy in which an electrophile derived from a flavan-3-ol peracetate is condensed with 1.5 eq. of a benzylated nucleophile. We demonstrate here the synthesis of procyanidin B1, a (-)-epicatechin-(4β-8)-(+)-catechin dimer, to demonstrate the utility of this method. This strategy is applicable for the synthesis of various commercially available flavan-3-ol and various oligomeric flavonoids.
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