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Clay JM, Hesek D, Oliver AG, et al. Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal. J Org Chem. 2016;81(13):5705-9doi: 10.1021/acs.joc.6b00756.
Clay, J. M., Hesek, D., Oliver, A. G., Lee, M., & Fisher, J. F. (2016). Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal. The Journal of organic chemistry, 81(13), 5705-9. https://doi.org/10.1021/acs.joc.6b00756
Clay, Julia M, et al. "Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal." The Journal of organic chemistry vol. 81,13 (2016): 5705-9. doi: https://doi.org/10.1021/acs.joc.6b00756
Clay JM, Hesek D, Oliver AG, Lee M, Fisher JF. Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal. J Org Chem. 2016 Jul 01;81(13):5705-9. doi: 10.1021/acs.joc.6b00756. Epub 2016 Jun 23. PMID: 27281133.
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J Org Chem. 2016 Jul 01;81(13):5705-9. doi: 10.1021/acs.joc.6b00756. Epub 2016 Jun 23.

Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal.

The Journal of organic chemistry

Julia M Clay, Dusan Hesek, Allen G Oliver, Mijoon Lee, Jed F Fisher

Affiliations

  1. Lilly Research Laboratories, Eli Lilly and Company , Lilly Corporate Center, Indianapolis, Indiana 46285, United States.
  2. Department of Chemistry and Biochemistry, University of Notre Dame , Notre Dame, Indiana 46556, United States.

PMID: 27281133 DOI: 10.1021/acs.joc.6b00756

Abstract

The buffered permanganate oxidation of (-)-myternal, a member of the pinene family, provides the α-hydroxyketone (-)-(1R,3S,5R)-3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one in preparative yield (65% on a multigram scale). This α-hydroxyketone is oxidized, in a second reaction, to the α,β-diketone (1R,5R)-6,6-dimethylbicyclo[3.1.1]heptane-2,3-dione ("PinDione"). As both oxidations are fast, simple, safe, inexpensive, good-yielding, and multigram scalable, these transformations are a preparative expansion of the pinane family.

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