Preliminary Studies on the Stereochemistry of Emetine. I. Mercuric Acetate Dehydrogenation of (-)-2'-Acylemetines

Abstract

Mercuric acetate dehydrogenation of (-)-2'-acylemetines, which have the same configuration as (-)-emetine, was found to afford 5, 11b-dehydro-2'-acylemetines. In preliminary experiments, it was shown that 1-alkyl-1, 2, 3, 4-tetrahydroisoquinoline derivatives are dehydrogenated with the same reagent to afford 3, 4-dihydro compounds, but the corresponding 2-acyl compounds resisted similar dehydrogenation. These results seem to strongly support Openshaw's view about the structure of tetradehydroemetine.