Synthesis of 3-Benzyloxy-6-methyl-7-methoxyphenanthrene-9-carboxaldehyde with Utilize Intramolecular Heck Reaction as the Key Step

The substituted phenanthrene-9-carboxyaldehydes are very important intermediates for the syntheses of phenanthroindolizidine and phenanthroquinolizidine alkaloids. The novel title compound was prepared from the reaction of 5 steps starting from the condensation of 3-methoxyl-4-methyl-phenylacetic acid and 4-(benzyloxy)-2-iodo-benzaldehyde, followed by esterification, cyclization, reduction, and oxidation. A new method for the preparation of phenanthrene ring via palladium-catalyzed intramolecular Heck reaction was described. The title compound was characterized by IR, 1H NMR, 13C NMR, elemental analysis, and MS.