Martin Lang - An Effective Method for the Synthesis of 13C-Labeled Polyprenylhydroxybenzoic Acids

Version 1

      Publication Details (including relevant citation   information):

      Martin Lang, Wolfgang Steglich

      Synthesis 2005, 1019-27

      Abstract:

      The synthesis of side-chain 13C-labeled   geranylgeranyl-4-hydroxybenzoic acids and   geranylgeranyl-3,4-dihydroxybenzoic acids is described. The   synthesis starts from O-protected methyl   hydroxyiodobenzoates, which are transformed into Grignard   reagents by low-temperature iodine-magnesium exchange according   to Knochel’s procedure. Copper catalyzed cross-coupling with   13C-labeled geranylgeranyl bromide followed by deprotection   affords the products with good yields and full retention of   stereochemistry.

      Address (URL): http://dx.doi.org/10.1055/s-2005-861863