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Communication | Special issue | Vol 8, No. 1, 1977, pp.97-102
Published online, 1st January, 1970
DOI: 10.3987/S(S)-1977-01-0097
Synthesis of a Benzo[a]phenanthridine Isomeric with Apomorphine

Chung-Chen Wei and Sidney Teitel*

*The Department of Chemistry Research, Hoffman-La Roghe Inc., Nutley, New Jersey 07110, U.S.A.


The synthesis of the benzo[a]phenanthridine (2), an isomer of apomorphine (1) with the identical rigid spatial arrangement of the dopamine moiety, is described. Conversion of the β-tetralone (9) into the N-benzoyl enamine (10) followed by photolysis furnished the trans-lactam (11) which was reduced, N-methylated and O-demethylated to afford the target compound (2).