Preparation of the intermediate aryl triflate (V) is shown is Scheme 29890101a. The dilithiated derivative of 4-bromo-3,5-dichlorophenol (I) is condensed with 2-adamantanone (II) to produce the carbinol adduct (III). Reduction of the tertiary alcohol of (III) by means of concentrated HI in boiling AcOH leads to the adamantanyl phenol (IV). This is then reacted with trifluoromethanesulfonic anhydride in cold pyridine to yield sulfonate (V).
Alkylation of cyclohexyl ethylamine (VI) with propargyl bromide (VII) gives the tertiary amine (VIII). Then, palladium-catalyzed coupling between the propargylic amine (VIII) and aryl triflate (V) furnishes the disubstituted acetylene derivative (IX). Finally, semihydrogenation of the triple bond of (IX) in the presence of cyclohexene and Lindlar catalyst gives rise to the target cis-olefin.