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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1595-1602
Published online, 15th October, 2013
DOI: 10.3987/COM-13-S(S)103
Development of a New Synthetic Strategy for Procyanidin Dimer Condensation Using Peracetylated Electrophiles

Sayaka Ishihara, Syoma Doi, Kota Harui, Taisuke Okamoto, Shuhei Okamoto, Joji Uenishi, Takashi Kawasaki, Noriyuki Nakajima,* and Akiko Saito*

*Department of Biotechnology, Faculty of Engineering, Toyama Prefectural University, 5180 Kurokawa, Kosugi, Toyama 939-0398, Japan


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.