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

Tools

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 (https://doi.org/10.1002/jlcr.3832)

[thumbnail of Queen-etal-JLCR-2020-Synthesis-of-3H-and-14C]
Preview
 Text. Filename: Queen_etal_JLCR_2020_Synthesis_of_3H_and_14C.pdf
Accepted Author Manuscript
Download (673kB)| Preview

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.

ORCID iDs

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
    Dates:
    Date
    Event
    30 April 2020
    Published
    4 February 2020
    Published Online
    31 January 2020
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:25 Feb 2020 15:22
    Last modified:27 Nov 2024 23:04
    URI:https://strathprints.strath.ac.uk/id/eprint/71560
CORE (COnnecting REpositories)