Vicinal tricarbonyls in synthesis. New routes to indolizidines.

Abstract

The vinyl vicinal tricarbonyl system 1 (VTC) has been used in two different approaches to prepare functionalized indolizidines. In one approach, 1 is used as a trielectrophile in reactions with primary amines possessing auxiliary donor sites. In a second approach, 1 is converted to a substituted 3-hydroxypyrrole-2-carboxylate. This pyrrole derivative then undergoes an intramolecular alkylation to give the indolizidine ring system.