合成路线1

Suzuki coupling of 3-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (I) with 4-methylphenylboronic acid (II) by means of palladium tetrakis(triphenylphosphine) gave (III). Subsequent refluxing of (III) with dimethyl carbonate in the presence of NaOMe afforded ketoester (IV). This was reduced with NaBH4 to give hydroxy ester (V), which was then dehydrated and hydrolyzed to the unsaturated acid (VI) with HCl in diglyme at 100 C. Alternatively, ketone (III) was carboxylated under CO2 atmosphere in the presence of either potassium carbonate or potassium tert-butoxide. The resulting ketoacid (VII) was reduced to hydroxyacid (VIII) with NaBH4, and then dehydrated to (VI) using 80% formic acid at 100 C. Carboxylic acid (VI) was then converted to the corresponding acid chloride (IX) by means of oxalyl chloride in CH2Cl2.