Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy

The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by two different cyclizations is described. The complete regioselectivity is controlled by the C4 Pictet–Spengler cyclization, in which an iminium ion acts as a transient directing (TDG) group. Furthermore, carbolines were co...

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Detalles Bibliográficos
Autores principales: Itoh, Tomoki, Chiba, Yuusuke, Kawaguchi, Shunsuke, Koitaya, Yuki, Yoneta, Yuuma, Yamada, Koji, Abe, Takumi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9062488/
https://www.ncbi.nlm.nih.gov/pubmed/35520921
http://dx.doi.org/10.1039/c9ra02321f
Descripción
Sumario:The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by two different cyclizations is described. The complete regioselectivity is controlled by the C4 Pictet–Spengler cyclization, in which an iminium ion acts as a transient directing (TDG) group. Furthermore, carbolines were constructed by a new Bischler–Napieralski-type cyclization, in which an unprecedented trichloromethyl carbamate serves as a reactive group.

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