Reaction of 2,2-dimethyl-6-hydroxymethylenecyclohexanone ( 10) with hydroxylamine hydrochloride produces a mixture of the isomeric isoxazoles 11 and 13. The less predominant of these ( 13) is the exclusive product from reaction of hydroxylamine hydrochloride with the isopropyl enol ether of 10, and is converted by methoxide into 6-cyano-2,2-dimethylcyclohexanone ( 16). This cyano ketone ( 14) reacts with methyl vinyl ketone and base to form 10-cyano-4,4-dimethyl-Δ 5-7-octalone ( 16), which is hydrogenated exclusively to the corresponding trans-7-decalone. The 8-hydroxymethylene derivative of octalone 16 is oxidized by 2,3-dichloro-5,6-dicyanoquinone to 10-cyano-4,4-dimethyl-8-formyl-Δ 5,8-7-hexalone ( 20). The latter reacts with the sodium enolate of ethyl acetoacetate at both C-9 and C-5 to produce the tricyclic adduct 25, but with t-butyl acetoacetate it undergoes Michael addition only at C-9. Treatment of the resulting adduct 21 with p-toluenesulfonic acid brings about cleavage of the t-butyl group, decar☐ylation, and aldol cyclodehydration to produce the tricyclic dienedione 22. Dehydrogenation of the latter with dichlorodicyanoquinone produces the title keto phenol 23. This sequence is a model for synthesis of various C-aromatic tricyclic diterpenoids.