Abstract
Synthesis and separation of the four stereoisomers of 2-methyl-4-[( R)-2-endo-bornyl]cyclohexanone by preparative high-performance liquid chromatography is described. The structure of these compounds is confirmed by their mass, proton magnetic resonance, and circular dichroism spectra, and also by means of isomerization of the axial α-methyl group in the cyclohexanone ring to an equatorial position. Only ( R)-2-methyl-( R)-4-[( R)-2-endobornyl]cyclohexanone is found to have a “urinous” odor.
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