Asymmetric Synthesis of Homocitric Acid Lactone

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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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
StatePublished - Nov 18 2016

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Lactones
Hydrogen
Carbon
Oxidation
homocitric acid
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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

Asymmetric Synthesis of Homocitric Acid Lactone. / Nickerson, Leslie A.; Huynh, Valerie; Balmond, Edward I.; Cramer, Stephen P.; Shaw, Jared T.

In: Journal of Organic Chemistry, Vol. 81, No. 22, 18.11.2016, p. 11404-11408.

Research output: Contribution to journalArticle

Nickerson, LA, Huynh, V, Balmond, EI, Cramer, SP & Shaw, JT 2016, 'Asymmetric Synthesis of Homocitric Acid Lactone', Journal of Organic Chemistry, vol. 81, no. 22, pp. 11404-11408. https://doi.org/10.1021/acs.joc.6b01997
Nickerson LA, Huynh V, Balmond EI, Cramer SP, Shaw JT. Asymmetric Synthesis of Homocitric Acid Lactone. Journal of Organic Chemistry. 2016 Nov 18;81(22):11404-11408. https://doi.org/10.1021/acs.joc.6b01997
Nickerson, Leslie A. ; Huynh, Valerie ; Balmond, Edward I. ; Cramer, Stephen P. ; Shaw, Jared T. / Asymmetric Synthesis of Homocitric Acid Lactone. In: Journal of Organic Chemistry. 2016 ; Vol. 81, No. 22. pp. 11404-11408.
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