New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates
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Date
Authors
Riley, Darren Lyall
Michael, Joseph P.
De Koning, Charles B.
Journal Title
Journal ISSN
Volume Title
Publisher
Beilstein-Institut
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.
Description
Supporting Information File 1
Experimental procedures and copies of NMR spectra.
Keywords
Alkaloid, Enaminone, Epitashiromine, Indolizidine, Tashiromine
Sustainable Development Goals
Citation
Riley, D.L., Michael, J.P. & De Koning, C.B. New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates. Beilstein Journal of Organic Chemistry. 2016, 12, 2609–2613.
DOI: 10.3762/bjoc.12.256.