923565-06-4Relevant articles and documents
From the gold-catalysed benzylation of arenes to the regio- and stereoselective synthesis of procyanidins dimers
Fabre, Sandy,Gueroux, Marie,Nunes, Emeline,Szlosek-Pinaud, Magali,Pianet, Isabelle,Fouquet, Eric
, p. 3045 - 3051 (2015/05/04)
This work reports on a new intermolecular C-C coupling reaction between electron rich arenes and benzylic alcohols or ethers, catalysed by gold(III) salts, or other catalysts such as gold(I) and iron (III), and its application to the regio- and stereoselective synthesis of procyanidins dimers B1 and B3.
An improved synthesis of procyanidin dimers: Regio- and stereocontrol of the interflavan bond
Tarascou, Isabelle,Barathieu, Karine,Andre, Yann,Pianet, Isabelle,Dufourc, Erick J.,Fouquet, Eric
, p. 5367 - 5377 (2007/10/03)
A direct and general synthesis of procyanidin dimers B1, B2, B3 and B4 (10a-d) is presented. The approach is based on the stoichiometric coupling of two protected monomeric units (the nucleophilic 2a-b and electrophilic 4a-b partners) and deals with the regio- and stereocontrol of the C4-C8 interflavan bond as well as the control of the degree of oligomerization. The synthesis involves a five-step pathway starting from the native catechin (1a) or epicatechin (1b) to the fully deprotected dimers 10a-d. Furthermore, the process appears to be iterative as the coupling intermediates 9a-d themselves can be readily used in further selective syntheses of trimers or higher oligomers. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
