合成路线1

The target compound has been obtained as follows: The condensation of 3-furoic acid (XV) with ethyl 3-iodopropionate (XVI) by means of Zn-Cu and Pd(PPh3)4 in hot benzene, followed by hydrolysis with NaOH in methanol/THF/water gives 4-(3-furyl)-4-oxobutyric acid (XVII), which is condensed with 3-methoxybenzaldehyde (XVIII) by means of NaOAc in hot Ac2O yielding the lactone (XIX). The cyclization of (XIX) by means of H2SO4 in methanol or HCl/methanol/AcOH affords 4-(3-furyl)-7-methoxynaphthalene-2-carboxylic acid methyl ester (XX), which is converted into the 7-hydroxy-4-(3-furyl)naphthalene-2-carbonitrile (XXI) by reaction with (Me)2Al-NH2 in refluxing toluene, followed by demethylation with pyridine and TFAA or HCl in dioxane. Finally, the condensation of naphthol (XXI) with benzyl alcohol derivative (XXII) by means of triphenylphosphine and diethyl azodicarboxylate (DEAD) or di-tert-butyl azodicarboxylate (DBAD) in THF affords the target product. The benzyl alcohol derivative (XXII) has been obtained as follows: The condensation of the bicyclic ketone intermediate (IV) with the 3-(tert-butyldiphenylsilyloxymethyl)phenyllithium (XXIII) gives the silylated benzyl alcohol (XXIV), which is finally deprotected with TBAF to afford the intermediate (XXII).