Stereochemical Studies of Monoterpene Compounds. VI. The Stereochemistry of 2-Hydroxypinocamphone and Its Reduction Products

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Abstract
The stereochemical structure of (+)-2-hydroxypinocamphone (II), which was obtained from (−)-α-pinene (I) by the permanganate oxidation, was examined by a combination of physicochemical methods. It was thus found that the C-2 methyl group is trans with respect to the C-6 bridge and that the preferred conformation is V having an axial hydroxyl group. In addition, the preferred conformation of cis-α-pinene glycol (IX) and trans-α-pinene glycol (X), which were produced from II by the lithium aluminum hydride reduction, was found to be IXa and Xa respectively.