A highly stereoselective asymmetric synthesis of (--)-lobeline and (--)-sedamine.
A highly stereoselective asymmetric synthesis of (--)-sedamine and (--)-lobeline is described from benzaldehyde in 16 and 17 steps with an overall yield of 20% and 14%, respectively. The key intermediate syn-3,4-epoxyalcohol was prepared in a highly diastereomeric fashion (>99% ee, dr) and served as a common intermediate for both alkaloids.
Felpin
François-Xavier
FX
Laboratoire de Synthèse Organique, Faculté des Sciences et des Techniques, CNRS UMR 6513, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
Lebreton
Jacques
J
D000470:Alkaloids / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D029746:Lobelia / Q000737:chemistry; D008120:Lobeline / Q000032:analysis / Q000138:chemical synthesis*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010880:Piperidines / Q000032:analysis / Q000138:chemical synthesis*; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; C459239:sedamine; D008120:Lobeline