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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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Detalles Bibliográficos
Autores principales: Riley, Darren L, Michael, Joseph P, de Koning, Charles B
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238587/
https://www.ncbi.nlm.nih.gov/pubmed/28144330
http://dx.doi.org/10.3762/bjoc.12.256
Descripción
Sumario: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.