合成路线1

The condensation of 4-hydroxybenzyl alcohol (I) with nitrocyclopentane (II) by means of TBAF at 130 C gives 4-(1-nitrocyclopentylmethyl)phenol (III), which is reduced to the corresponding amine (IV) with hydrogen over Raney-Ni in methanol. The protection of the NH2 group of (IV) with di-tert-butyl dicarbonate affords the carbamate (V), which is condensed with the phosphinic ester (VI) by means of NaH in DMF giving the substituted phosphinate (VII). The elimination of the carbamate group of (VII) with TFA in dichloromethane yields the cyclopenatylamine (VIII), which is condensed with the chiral oxirane (IX) in refluxing methanol affording the substituted aminopropanol (X). Elimination of the benzyl protecting group of (X) gives the intermediate phosphinic ester (XI) that is finally hydrolyzed with LiOH in methanol.