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A Route to the C,D,E Ring System of the Aspidosperma Alkaloids

[Image: see text] A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product...

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Detalles Bibliográficos
Autores principales: Giampa, Geoffrey M., Fang, Jian, Brewer, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4994716/
https://www.ncbi.nlm.nih.gov/pubmed/27500799
http://dx.doi.org/10.1021/acs.orglett.6b01674
Descripción
Sumario:[Image: see text] A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis acid to give an iminium product that can be directly reduced to the corresponding amine.