An effective enantioselective approach to the securinega alkaloids: total synthesis of (-)-norsecurinine.
[reaction: see text] A highly versatile approach to the enantioselective synthesis of securinega alkaloids is presented. Crucial steps are a palladium-catalyzed enantioselective imide alkylation, a vinylogous Mannich reaction, and a ring-closing metathesis process. Through this strategy, the synthesis of (-)-norsecurinine has been accomplished in nine steps and 11% overall yield.
Alibés
Ramón
R
Universitat Autonoma de Barcelona, Departament de Química, Bellaterra, Spain.
Bayón
Pau
P
de March
Pedro
P
Figueredo
Marta
M
Font
Josep
J
García-García
Elena
E
González-Gálvez
David
D
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D019665:Euphorbiaceae / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D010880:Piperidines; C050244:norsecurinine