Study of the intramolecular cyclization of N-methyl-3-phenyl-N-(2-(E)-phenylethenyl)-trans(cis)-oxiranecarboxamide – Syntheses of Homoclausenamide and Dehydroclausenamide

Homoclausenamide was synthesized for the first time, and the intramolecular cyclization study of N-methyl-3-phenyl-N-(2-(E)-phenylethenyl)-trans(cis)-oxiranecarboxamide well demonstrated how the stereochemistry affects the cyclization paths.

Under Lewis acid condition, compound 8 undergoes cyclizations to give Homoclausenamide and Dehydroclausenamide.Figure optionsDownload as PowerPoint slide