CONVERSION OF DELTA-(SULFONYL)AMINO-ALPHA-EPOXY KETONES TO BICYCLIC KETOPYRROLES VIA INTRAMOLECULAR CONJUGATE-ADDITION TO AZOENE INTERMEDIATES - SYNTHESIS OF THE BICYCLIC KETOPYRROLE CORE OF THE 1-AZAFULVENE ROSEOPHILIN

摘要

Reaction of delta-(sulfonyl)amino-alpha-epoxy ketones with dimethylhydrazine results in cyclization to pyrrolidine-fused beta-hydroxy dimethylhydrazones. elimination affords dihydropyrroles which can be converted to sulfonyl-protected ketopyrroles via oxidation with NIS; alternatively, treatment with DBU affords N-H bearing ketopyrroles. Copyright (C) 1996 Elsevier Science Ltd [References: 21]