Total synthesis of the reported structure of 13a-hydroxytylophorine

The first total synthesis of the reported structure of 13a-hydroxytylophorine was accomplished. The key step was an unprecedented NaBH(4)-promoted one-pot reductive cyclization cascade that efficiently yielded a hydroxyl azonane intermediate. The indolizidine framework was obtained by means of oxida...

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Detalles Bibliográficos
Autores principales: Zhang, Hui, Li, Gang, Su, Bo, Deng, Meng, Liu, Yu-Xiu, Gu, Yu-Cheng, Wang, Qing-Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5716997/
https://www.ncbi.nlm.nih.gov/pubmed/29208905
http://dx.doi.org/10.1038/s41598-017-17015-8
Descripción
Sumario:The first total synthesis of the reported structure of 13a-hydroxytylophorine was accomplished. The key step was an unprecedented NaBH(4)-promoted one-pot reductive cyclization cascade that efficiently yielded a hydroxyl azonane intermediate. The indolizidine framework was obtained by means of oxidation and a subsequent unexpected protecting-group migration. This total synthesis revealed that the reported structure of the naturally isolated compound is incorrect.

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