Total synthesis of 14C-labeled procyanidin B2

Florian Viton, Cyrille Landreau, David Rustidge, Gill Little, Fabien Robert, Gary Williamson, Denis Barron

Research output: Contribution to journalArticleOtherpeer-review


During the last decades, many in vitro and in vivo studies have shown the beneficial effects on health of procyanidins. However, their absorption and metabolism is still not fully understood and some aspects are still controversial. In order to have a clearer picture of the metabolism of procyanidins, the use of labelled compounds is essential. In this context, the enantioselective synthesis of 14C-radiolabelled procyanidin B2 was developed in our laboratories. It was achieved in fourteen 'hot' steps, involving as key steps the Sharpless dihydroxylation of an elaborated alkene, a stereoselective intramolecular cyclization to benzylated (+)-catechin and the condensation of two (-)-epicatechin units. 11 mCi of protected procyanidin B2 were obtained from 524 mCi of potassium [14C]cyanide.

Original languageEnglish
Pages (from-to)371-374
Number of pages4
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Issue number5-6
Publication statusPublished - 1 May 2010
Externally publishedYes


  • Carbon-14C
  • Catechins
  • Polyphenols
  • Procyanidins
  • Radiolabeled synthesis

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