合成路线1

The synthesis of intermediate (XI) as been performed as follows: The reaction of 3-benzyloxy-5-methoxystyrene (I) with K2OsO4(OH)4, (DHQ)2PHAL and BocNClNa gives the hydroxyethyl carbamate (II), which is protected with Mem-Cl, yielding (III). The reductive deprotection of (III) with H2 over Pd/C, followed by reaction with trifluoroacetic anhydride (TFAA), affords the amide (IV), which is condensed with the hydroxyethyl carbamate (V) (obtained by reaction of 3-fluoro-4-nitrostyrene (VI) with K2OsO4(OH)4, (DHQD)2PHAL and BocNClNa) by means of K2CO3, providing the diaryl ether (VII). The reduction of the nitro group of (VII) with H2 over Pd/C gives the corresponding amino group, which is converted into the phenol (IX) by reaction with tBu-ONO, BHF4, Cu2O and Cu(NO3)2. The methylation of the phenol (IX) with MeI and K2CO3 yields the corresponding ether (X), which is finally treated with K2CO3 to eliminate the trifluoroacetyl group, yielding the desired intermediate (XI).