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Paper | Regular issue | Vol 68, No. 5, 2006, pp.993-1006
Published online, 24th March, 2006
DOI: 10.3987/COM-06-10710
■ A Convenient Synthesis of Papaverine Analogs via Photocyclization of N-Acyl-α-dehydroarylalaninamide Derivatives

Hideki Hoshina, Kei Maekawa, Kaori Kobayashi, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

Photochemical cyclizations of (Z)-N-(substituted phenylacetyl)-α- dehydro(3,4-dimethoxyphenyl)alaninamides in methanol were found to proceed regioselectively giving papaverine analogs in satisfactory yields, irrespective of the substituent introduced. MM2 and PM5 calculations revealed that steric hindrance of the methoxy group introduced at the meta-position on the styryl benzene ring is responsible for the regioselective photocyclization observed.