New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates (Beilstein Journal of Organic Chemistry)

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. Beilstein J. Org. Chem. 2016, 12, 2609–2613. doi:10.3762/bjoc.12.256