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

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

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...

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Veröffentlicht in:Beilstein journal of organic chemistry 2016-12, Vol.12 (1), p.2609-2613
Hauptverfasser: Riley, Darren L, Michael, Joseph P, de Koning, Charles B
Format: Artikel
Sprache:eng
Schlagworte:
alkaloid
Chemistry
enaminone
epitashiromine
Full Research Paper
indolizidine
tashiromine
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Zusammenfassung: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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.12.256