660832-10-0Relevant academic research and scientific papers
Development of a new synthetic strategy for procyanidin dimer condensation using peracetylated electrophiles
Ishihara, Sayaka,Doi, Syoma,Harui, Kota,Okamoto, Taisuke,Okamoto, Shuhei,Uenishi, Joji,Kawasaki, Takashi,Nakajima, Noriyuki,Saito, Akiko
, p. 1595 - 1602 (2014)
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.
Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4B,8)-epicatechin or -catechin dimers and their digallates
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Page/Page column 7, (2010/11/25)
Improved processes for the preparation of tetra-O-benzyl protected catechin, for the coupling of the tetra-O-benzyl protected catechin or epicatechin with a C-4 activated, tetra-O-benzyl protected epicatechin for the galloylation of the epicatechin-(4β,8)-catechin or -epicatechin dimer-the dimer digallates, and for the deprotection (i.e., debenzylation) of the protected epicatechin dimers and protected epicatechin dimer digallates are disclosed.
