The tosylation of the primary alcohol of the hexahydroindenepropanol (I) with TsCl in pyridine gives the tosylate (II), which is treated with NaCN in DMSO to yield the butyronitrile (II). The reduction of (III) with diisobutylaluminum hydride in dichloromethane affords the butyraldehyde (IV), which is condensed with CBr4 by means of Zn in dichloromethane providing the 1,1-dibromo-1-pentene derivative (V). The dehydrobromination of (V) with n-BuLi in THF/hexane affords the 1-pentyne derivative (VI), which is treated with 1-(trimethylsilyl)imidazole to give the silyl ether (VII). The condensation of (VII) with acetone by means of n-BuLi in THF yields the 3-heptyn-2-ol derivative (VIII), which is desilylated with TBAF in THF affording the diol (IX). The oxidation of the secondary alcohol of (IX) with bipyridinium chlorochromate (BPCC) in dichloromethane provides the corresponding ketone (X), which is protected at the tertiary alcohol with 1-(trimethylsilyl)imidazole giving the silylated ketone (XI). The condensation of (XI) with the phosphorane (XII) by means of n-BuLi in THF yields the protected intermediate (XIII), which is finally deprotected with TBAF in THF.

Alternatively, the intermediate diol (IX) has been obtained as follows: The condensation of perhydroindene derivative (XIV) with the acetylenic aldehyde (XV) by means of Me3AlCl gives the acetylenic alcohol (XVI), which is esterified to the formate (XVII) or the carbonate (XVIII). The deoxygenation of (XVII) or (XVIII) by means of Pd(acac)2 and P(CH3)3 in hot toluene affords the silylated diol (XIX), which is submitted to desilylation with TBAF to afford the target diol intermediate (IX).