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Report | Regular issue | Vol 20, No. 12, 1983, pp.2417-2424
Published online, 1st January, 1970
DOI: 10.3987/R-1983-12-2417
■ Synthesis of 6’-Methylated Reticulines and Tetrahydropapaverolines

Padam N. Sharma, Kenner C. Rice, and Arnold Brossi

*Section on Medical Chemistry, Bldg.4, Room 135, Metabolism and Digestive and Kideny Deseases, National Institute of Health, Bethesda, MD 20892, U.S.A.

Abstract

Racemic 6’-methylreticuline and the racemate and both enantiomers of 6’-methyl-N-norreticuline and 6’-methyltetrahydropapaveroline were synthesized from the appropriate isomers of coreximine diacetate (1). Reduction of crystalline chloromethylcarbamate 2 with LAH gave (±)-6’-methylreticuline (5) directly. Hydrogenation (±)-2 and the optical isomers followed by hydrazinolysis provided the corresponding. 6’-methyl-N-norreticulines (6, 6a, 6b) which were converted to the racemate and enantiomers of 6’-methyltetrahydropapaveroline (8, 8a, 8b) by O-demethylation with 48% hydrobromic acid.