title: Stereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction.
abstract: Starting from (-)-acetoxyglutarimide, the enantioselective multistep synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine has been demonstrated via a common hydroxyl-lactam intermediate with very good overall yields. The acetoxy function from (-)-acetoxyglutarimide was initially used as a handle to induce enantioselectivity and then as a latent source of the ketone carbonyl group. Most importantly, substrate dependent reversal of the diastereoselectivity in ester aldol reactions of hexahydroindolo[2,3-a]quinolizinones has been reported.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India. np.argade@ncl.res.in.
authors.forename: Pravat
authors.initials: P
authors.lastname: Mondal
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India. np.argade@ncl.res.in.
authors.forename: Narshinha P
authors.initials: NP
authors.lastname: Argade
mesh_terms: D060326:Chemistry Techniques, Synthetic; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D014749:Vincamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C000626147:3-epitacamonine; D026121:Indole Alkaloids; D007659:Ketones; C000626146:desethyleburnamonine; D014749:Vincamine; C044616:vindeburnol