Synthesis of [3H] and [14C]genipin

Queen, Adele E. and Hesk, David and Lindsay, David M. and Kerr, William J. and Rehder, Kenneth and Fennell, Tim and Mascarella, Wayne and Zhong, Desong and Runyon, Scott (2020) Synthesis of [3H] and [14C]genipin. Journal of Labelled Compounds and Radiopharmaceuticals, 63 (4). pp. 196-202. ISSN 0362-4803

[img] Text (Queen-etal-JLCR-2020-Synthesis-of-3H-and-14C)
Queen_etal_JLCR_2020_Synthesis_of_3H_and_14C.pdf
Accepted Author Manuscript
Restricted to Repository staff only until 4 February 2021.
Download (673kB) | Request a copy from the Strathclyde author

    Abstract

    [3H]Genipin was synthesized in a single step by Ir(I) catalyzed hydrogen isotope exchange. Conditions for selective exchange of the sp2 CH bond ortho to the methyl ester functionality were developed through deuterium modeling studies through a catalyst screen. Optimized conditions so obtained were then utilized with tritium gas to generate [3H]genipin at a specific activity of 18.5 Ci/mmol. Racemic [14C]genipin was prepared in eight steps in overall 5.4% radiochemical yield from potassium [14C]cyanide.

    Creators(s): Queen, Adele E., Hesk, David, Lindsay, David M. ORCID logoORCID: https://orcid.org/0000-0003-4498-5094, Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Rehder, Kenneth, Fennell, Tim, Mascarella, Wayne, Zhong, Desong and Runyon, Scott;
    Item type:Article
    ID code:71560
    Keywords:carbon-14, gardenia blue, genipin, Iridium (I), Otera's catalyst, tritium, Chemistry, Chemistry(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:25 Feb 2020 15:22
    Last modified:21 Jan 2021 11:45
    URI:https://strathprints.strath.ac.uk/id/eprint/71560
    Export data:
    CORE (COnnecting REpositories)