合成路线1

Synthesis of the aromatic intermediate (XXXIII): The esterification of the 5-hydroxyisophthalic acid (XVII) with SOCl2 and methanol gives the dimethyl ester (XVIII), which is treated with allyl bromide (XIX) and K2CO3 in refluxing acetone to yield the allyl ether (XX). The thermal isomerization of (XX) affords 4-allyl-5-hydroxyisophthalic acid dimethyl ester (XXI), which is treated with Bn-Br and K2CO3 in refluxing acetone to provide the benzyl ether (XXII). The hydrolysis of the ester groups of (XXII) with NaOH in THF gives the isophthalic acid (XXIII), which by reaction with Br2 and NaHCO3 yields the lactone (XXIV). The reduction of the carboxyl group of (XXIV) with isopropyl chloroformate and NaBH4 in THF/water affords the carbinol (XXV), which is protected with Bom-Cl and DIEA, providing compound (XXVI). The debromination of (XXVI) with Zn and NH4Cl in ethanol/water gives the 2-allylbenzoic acid (XXVII), which by a Curtius rearrangement with DPPA and TEA in refluxing tert-butanol yields the aryl carbamate (XXVIII). The reaction of (XXVIII) with OsO4 and NaIO4 in dioxane/water affords the indoline derivative (XXIX), which is treated with NaBH4 in EtOH to afford the 2-phenylethanol derivative (XXX). The reaction of (XXX) with Tbdms-Cl, TEA and DMAP provides the silyl ether (XXXI), which is treated with Tbdms-OTf and pyridine to give the aniline derivative (XXXII). Finally, this amine is reprotected with Alloc-Cl and NaHCO3 to yield the desired intermediate (XXXIII).