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Total synthesis of aristolactam alkaloids via synergistic C–H bond activation and dehydro-Diels–Alder reactions

A concise total synthesis of aristolactam alkaloids by a synergistic combination of C–H bond activation and dehydro-Diels–Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneis...

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Detalles Bibliográficos
Autores principales: Reddy, Mallu Chenna, Jeganmohan, Masilamani
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100235/
https://www.ncbi.nlm.nih.gov/pubmed/30155216
http://dx.doi.org/10.1039/c7sc00161d
Descripción
Sumario:A concise total synthesis of aristolactam alkaloids by a synergistic combination of C–H bond activation and dehydro-Diels–Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones via a ruthenium-catalyzed C–H bond activation, and a dehydro-Diels–Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benzynes, were developed. The method presented allows the opportunity for the construction of all the rings of aristolactams from easily available starting materials.