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Ensemble of Pinanones From the Permanganate Oxidation of Myrtenal

Ensemble of Pinanones From the Permanganate Oxidation of Myrtenal

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

J Org Chem. 2016 Jul 1;81(13):5705-9.

PMID: 27281133

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18486696	(1R)-(−)-Myrtenal		18486-69-6	Price

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