2,2,3,6-Tetramethylcyclohexanone → (-)-(3R,5R,8R)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane

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Reaction Steps

Prepared according to the general method described, starting from 2,2,3,6-tetramethyl-1-cyclohexanone (mixture trans/cis: 85/15%) under the conditions described in published European patent application No. 0 374 509. The analytical data for this epoxide are described therein. When using as starting product (+)-(3S,6S)-2,2,3,6-tetramethyl-1-cyclohexanone ([α]20D =+52.2°) or, respectively (-)-(3R,6R)-2,2,3,6-tetramethyl-1-cyclohexanone ([α]20D =-50.7°), there were obtained the optically active isomers of the above-mentioned epoxide, i.e., (+)-(3S,5S,8S)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane ([α]20D =+36.0°) or, respectively (-)-(3R,5R,8R)-4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane ([α]20D =-35.1°). The analytical data of these compounds are also described in said European patent application.

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