An approach to the skeleton of the securinega alkaloids. The total synthesis of (+/-)-securinine.
[structure: see text]. The concise total synthesis of securinine in nine steps from readily available starting materials is described. Key steps of the synthesis include an addition of a silyloxyfuran to an in situ generated iminium ion and a novel ring closing metathesis reaction.
Liras
S
S
Pfizer Global Research and Development, Groton, Connecticut 06340, USA. spiros_liras@groton.pfizer.com
Davoren
J E
JE
Bordner
J
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D001381:Azepines; D000697:Central Nervous System Stimulants / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D018756:GABA Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings; D006572:Heterocyclic Compounds, Bridged-Ring; D007202:Indicators and Reagents; D007783:Lactones; D008958:Models, Molecular; D008968:Molecular Conformation; D010880:Piperidines; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D000697:Central Nervous System Stimulants; D018756:GABA Antagonists; D006576:Heterocyclic Compounds, 4 or More Rings; D006572:Heterocyclic Compounds, Bridged-Ring; D007202:Indicators and Reagents; D007783:Lactones; D010880:Piperidines; C000785:securinine