New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates

Abstract

The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.

Keywords

• alkaloid
• enaminone
• epitashiromine
• indolizidine
• tashiromine