合成路线1

Condensation of 1-tritylimidazole-4-carbaldehyde (IV) with ethyl acetate (XIII) using LDA in THF furnishes ethyl 3-hydroxy-3-(1-trityl-4-imidazolyl)propanoate (XIV), which by reduction with LiAlH4 in THF affords diol (XV). Selective oxidation of the secondary alcohol of compound (XV) by means of MnO2 in CH2Cl2 gives 3-hydroxy-1-(1-trityl-4-imidazolyl)-1-propanone (XVI), which upon hydroxyl group activation with MsCl and Et3N in EtOAc followed by cyclization in the presence of Et3N and MeOH in acetonitrile at 70 °C yields 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (XVII). Coupling of ketone (XVII) with metalated 6-bromo-N-methyl-2-naphthamide (XVIII) [prepared by amidation of 6-bromo-2-naphthoic acid (I) with CH3NH2 by means of EDC, HOBt and DIEA in DMF] with BuLi and optionally 2-bromobenzotrifluoride in THF provides the 7-(2-naphthyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-ol derivative (XIX), which is finally resolved by crystallization with (2S,3S)-(–)-tartranilic acid followed by addition of NaOH or by chiral HPLC separation .
Intermediate (XVI) can alternatively be prepared by addition of HBr to 1-(1-trityl-4-imidazolyl)-2-propen-1-one (XX) in AcOH to afford the bromoketone (XXI) and then cyclization in the presence of Et3N .