Reaction conditions are defined for the preparation of ketols by Robinson annelation of cyclohexanones. The cis-keto1 I1 and the trans-keto1 I11 are formed stereoselectively from 2-methylcyclohexanone and cyclohexanone using an equimolar quantity of methyl vinyl ketone. The ketol I1 is a convenient source of lO-methyl-l (9)-octalone-2 (I), The scope and stereochemistry of the Michael-aldol reaction sequence is discussed.
