title: Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions.
abstract: Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr ∼13-16:1) were obtained using lithium enolates of phenyl esters in combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.
authors: The School of Chemistry, The University of Southampton, Highfield, Southampton SO17 1BJ, UK.
authors: Amanda C
authors: AC
authors: Cutter
authors: Iain R
authors: IR
authors: Miller
authors: John F
authors: JF
authors: Keily
authors: Richard K
authors: RK
authors: Bellingham
authors: Mark E
authors: ME
authors: Light
authors: Richard C D
authors: RC
authors: Brown
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis*; D015394:Molecular Structure; D013034:Sparteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000093843:Quinolizidine Alkaloids
chemical_list: D000447:Aldehydes; D007097:Imines; D007212:Indolizines; D013034:Sparteine; C512155:tashiromine; C015971:lupinine; D000093843:Quinolizidine Alkaloids; C116609:3-hydroxybutanal