A new general access to either type of Securinega alkaloids: synthesis of securinine and (-)-allonorsecurinine.
The syntheses of securinine and (-)-allonorsecurinine have been achieved starting from easily available alpha-amino acid derivatives and using as key steps a RCM and a Heck reaction for the formation of rings D and C, respectively. [reaction: see text]
Alibés
Ramon
R
Departament de Química, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain.
Ballbé
Marta
M
Busqué
Félix
F
de March
Pedro
P
Elias
Laia
L
Figueredo
Marta
M
Font
Josep
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D019665:Euphorbiaceae / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines; C000785:securinine