A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkal...

Descripción completa

Detalles Bibliográficos
Autores principales: Jepsen, Tue Heesgaard, Glibstrup, Emil, Crestey, François, Jensen, Anders A, Kristensen, Jesper Langgaard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480346/
https://www.ncbi.nlm.nih.gov/pubmed/28684978
http://dx.doi.org/10.3762/bjoc.13.98
Descripción
Sumario:We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.

Ejemplares similares