Ensemble of Pinanones from the Permanganate Oxidation of Myrtenal

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• 作者：Julia M. Clay ; Dusan Hesek ; Allen G. Oliver ; Mijoon Lee ; Jed F. Fisher
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：81
• 期：13
• 页码：5705-5709
• 全文大小：270K
• 年卷期：0
• ISSN：1520-6904

文摘

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.