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This appears to require addition of –OH and –OCH₃ groups in an anti fashion to the double bond. Although this seems similar to KMnO₄ or OsO₄ hydroxylation, these reactions follow a syn-addition course, so something different is needed. Recalling that epoxides can be opened by nucleophile attack (S_N2) at one of the carbon atoms, a route to trans-oriented oxygen substituents can be planned. First, the cyclohexene must be epoxidized (reaction with a peracid), then the epoxide is opened by methoxide substitution at the least hindered carbon.

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Since ketones can be prepared by oxidation of 2º-alcohols, this transformation may be restated as the conversion of 1-methylcyclohexene to 2-methylcyclohexanol. This would require anti-Markovnikov addition of water to the double bond, so a hydroboration sequence is indicated.

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Here the ring is cleaved, leaving a chain of carbons. Among the reactions that could be used to achieve this are glycol cleavage and ozonolysis. Since the desired product is a diol, the carbonyl products of the initial cleavage must be reduced. Sodium borohydride (NaBH₄) is an excellent reagent for reducing aldehydes and ketones to alcohols.

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We need to attach a phenyl group to the six-membered ring. The carbonyl group has an electrophilic carbon atom, and this is known to form covalent bonds to a variety of nuclephiles. Since phenyllithium has a strongly nucleophilic phenyl group, it adds to cyclohexanone to give a phenyl substituted 3º-alcohol. Acid-catalyzed dehydration of this alcohol then gives the desired product.

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Here again we need to attach a phenyl group to the existing ring. Since there is no electrophilic carbon site on the ring, a reaction with phenyllithium will not take place. If the double bond is epoxidized two things are accomplished: (i) oxygen is introduced, and may eventually become part of the carbonyl group, & (ii) electrophilic sites are created, which may be attacked by phenyllithium. Thus reaction of cyclohexene oxide with phenyllithium give a 2º-alcohol, which may then be oxidized to the desired ketone.

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