Enantioselective synthesis of isotopically labeled homocitric acid lactone

Jared T. Moore, Nadine V. Hanhan, Maximillian E. Mahoney, Stephen P. Cramer, Jared T. Shaw

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically 13C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement.

Original languageEnglish (US)
Pages (from-to)5615-5617
Number of pages3
JournalOrganic Letters
Volume15
Issue number22
DOIs
StatePublished - Nov 15 2013

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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    Moore, J. T., Hanhan, N. V., Mahoney, M. E., Cramer, S. P., & Shaw, J. T. (2013). Enantioselective synthesis of isotopically labeled homocitric acid lactone. Organic Letters, 15(22), 5615-5617. https://doi.org/10.1021/ol402802g