title: 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.
authors.affiliation: Department of Chemistry, University of Pretoria, Pretoria 0028, South Africa; Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Wits 2050, Johannesburg, South Africa.
authors.forename: Darren L
authors.initials: DL
authors.lastname: Riley
authors.affiliation: Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Wits 2050, Johannesburg, South Africa.
authors.forename: Joseph P
authors.initials: JP
authors.lastname: Michael
authors.affiliation: Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Wits 2050, Johannesburg, South Africa.
authors.forename: Charles B
authors.initials: CB
authors.lastname: de Koning
keywords: alkaloid; enaminone; epitashiromine; indolizidine; tashiromine