Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal

The buffered permanganate oxidation of (-)-myternal, a member of the pinene family, provides the alpha-hydroxyketone (-)-(1R,3S,5R)-3-hydroxy-6,6-dimethylbicyclo [3.1.1]heptan-2-one in preparative yield (65% on a multigram scale). This alpha-hydroxyketone is oxidized, in a second reaction, to the alpha,beta-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.