Enantioselective total synthesis of virosaine A and bubbialidine.
The first enantioselective total syntheses of virosaine A and bubbialidine are described. Key transformations include the formation of a tetracyclic intermediate via an intramolecular aza-Michael addition, generation of a N-hydroxy-pyrrolidine through a Cope elimination and an intramolecular [1,3]-dipolar cycloaddition to generate a complex 7-oxa-1-azabicyclo[3.2.1]octane ring system.
Department of Chemistry, University of Basel, St. Johanns-Ring 19, Basel 4056, Switzerland.
Hideki
H
Miyatake-Ondozabal
Linda M
LM
Bannwart
Karl
K
Gademann
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D013237:Stereoisomerism; D013379:Substrate Specificity; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry*
D000970:Antineoplastic Agents; D014326:Tropanes; C582686:bubbialidine; C576140:virosaine A