Asymmetric Synthesis of Homocitric Acid Lactone

Leslie A. Nickerson, Valerie Huynh, Edward I. Balmond, Stephen P. Cramer, Jared T. Shaw

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4 Scopus citations

Abstract

A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.

Original languageEnglish (US)
Pages (from-to)11404-11408
Number of pages5
JournalJournal of Organic Chemistry
Volume81
Issue number22
DOIs
Publication statusPublished - Nov 18 2016

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ASJC Scopus subject areas

  • Organic Chemistry

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Nickerson, L. A., Huynh, V., Balmond, E. I., Cramer, S. P., & Shaw, J. T. (2016). Asymmetric Synthesis of Homocitric Acid Lactone. Journal of Organic Chemistry, 81(22), 11404-11408. https://doi.org/10.1021/acs.joc.6b01997