Final answer:
A multi-step synthesis plan for 1-phenylcyclohexane cis 1,2-diol from cyclohexanol could involve protection of the alcohol, phenylation, oxidation, stereospecific reduction, and finally deprotection to preserve the cis configuration of the diol.
Step-by-step explanation:
Synthesis of 1-phenylcyclohexane cis 1,2-diol
To synthesize 1-phenylcyclohexane cis 1,2-diol from cyclohexanol, we need to outline a multi-step synthetic route. The first step could involve the protection of the alcohol group in cyclohexanol using a suitable protecting group, potentially following a pathway similar to the preparation of (4R,5R)-4,5-O-isopropylidene-2-cyclopenten-1-ol provided in the preparative text. Protected cyclohexanol would then undergo phenylation to introduce the phenyl group.
After phenyl addition, an oxidation step is required to convert the cyclohexane derivative to a diol. This could mimic the stereospecific reduction mentioned in Scheme 1, adjusted to perform an oxidation using reagents like OsO4 or KMnO4, then followed by a stereospecific reduction to achieve the cis stereochemistry of the diol.
The deprotection of the 1,2-diol would then provide the final molecule, 1-phenylcyclohexane cis 1,2-diol. It is crucial that the protection and deprotection steps preserve the newly formed stereocenter to prevent any possible isomerization.