Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal

摘要

The buffered permanganate oxidation of (-)-myternal, a member of the pinene family, provides the alpha-hydroxyketone (-)-(1R,3S,5R)-3-hydroxy-6,6-dimethylbicyclo 3.1.1heptan-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-dimethylbicyclo3.1.1heptane-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.