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■ A Novel Cleavage of the Methlenedioxy Group during the Photochemical Synthesis of Aporphines

Bantwal R. Pai,* Hosbett Suguna, Sakaran Natarajan, and Govindarajan Manikumar

*Department of Chemistry, Presidency College, Madras 600005, India

Abstract

Irradiation of 1-(2-bromo-5-hydroxybenzyl)-1,2,3,4-tetrahydro-2-methyl-6,7-methylenedioxyisoquinoline (1) in 2% aqueous sodium hydroxide solution gives (±)-roemeroline (2) and 2,9-dihydroxyaporphine (3). Similarly 1-(2-bromo-5-hydroxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-2-methyl-6,7-methylenedioxyisoquinoline (5) leads to (±)-cassythicins (6) and 2,9-dihydroxy-10-methoxyaparphine (7). These are the first examples of the cleavage of methylenedioxy groups during photolysis in an alkaline medium.