DEVELOPMENT OF A NEW SYNTHETIC STRATEGY FOR PROCYANIDIN DIMER CONDENSATION USING PERACETYLATED ELECTROPHILES

作者:Ishihara Sayaka*; Doi Syoma; Harui Kota; Okamoto Taisuke; Okamoto Shuhei; Uenishi Joji; Kawasaki Takashi; Nakajima Noriyuki; Saito Akiko
来源:Heterocycles, 2014, 88(2): 1595-1602.
DOI:10.3987/COM-13-S(S)103

摘要

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-(4 beta-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.

  • 出版日期2014-1-1