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Merck
  • Synthesis of proanthocyanidins. Part 1. The first oxidative formation of the interflavanyl bond in procyanidins.

Synthesis of proanthocyanidins. Part 1. The first oxidative formation of the interflavanyl bond in procyanidins.

Organic letters (2008-08-06)
Matthew C Achilonu, Susan L Bonnet, Jan H van der Westhuizen
RESUMO

A novel and efficient method for the oxidative condensation of tetra-O-methyl-3-oxocatechin 4 with tetra-O-methylcatechin is described. Treatment of a solution of 3 (2 equiv) and 4 (1 equiv) with silver tetrafluoroborate readily affords the phenolic per-O-methyl ethers of 3-oxocatechin(4-8)-catechin 18 and 19. Subsequent metal hydride reduction provides access to procyanidin B-3 analogues with the 3,4-cis diastereomers predominating.

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Sigma-Aldrich
Silver tetrafluoroborate, 98%
Sigma-Aldrich
Silver tetrafluoroborate, ≥99.99% trace metals basis