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

5 Citations (Scopus)

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

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Carbon Isotopes
Ireland
carbon isotopes
Lactones
alcohols
routes
asymmetry
acids
synthesis
homocitric acid
allyl alcohol

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

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

Enantioselective synthesis of isotopically labeled homocitric acid lactone. / Moore, Jared T.; Hanhan, Nadine V.; Mahoney, Maximillian E.; Cramer, Stephen P.; Shaw, Jared T.

In: Organic Letters, Vol. 15, No. 22, 15.11.2013, p. 5615-5617.

Research output: Contribution to journalArticle

Moore, JT, Hanhan, NV, Mahoney, ME, Cramer, SP & Shaw, JT 2013, 'Enantioselective synthesis of isotopically labeled homocitric acid lactone', Organic Letters, vol. 15, no. 22, pp. 5615-5617. https://doi.org/10.1021/ol402802g
Moore JT, Hanhan NV, Mahoney ME, Cramer SP, Shaw JT. Enantioselective synthesis of isotopically labeled homocitric acid lactone. Organic Letters. 2013 Nov 15;15(22):5615-5617. https://doi.org/10.1021/ol402802g
Moore, Jared T. ; Hanhan, Nadine V. ; Mahoney, Maximillian E. ; Cramer, Stephen P. ; Shaw, Jared T. / Enantioselective synthesis of isotopically labeled homocitric acid lactone. In: Organic Letters. 2013 ; Vol. 15, No. 22. pp. 5615-5617.
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