title: Total synthesis of sedum alkaloids via catalyst controlled aza-Cope rearrangement and hydroformylation with formaldehyde.
abstract: The catalytic asymmetric aminoallylation of chiral aldehydes is developed as a new method for the catalyst controlled synthesis of syn- and anti-1,3-aminoalcohols. This methodology is highlighted in the synthesis of the sedum alkaloids (+)-sedridine and (+)-allosedridine both of which have their final carbon incorporated during closure of the piperidine ring via a hydroformylation with formaldehyde.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.
authors.forename: Hong
authors.initials: H
authors.lastname: Ren
authors.forename: William D
authors.initials: WD
authors.lastname: Wulff
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005557:Formaldehyde / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D031963:Sedum / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000605:Amino Alcohols; D010880:Piperidines; D005557:Formaldehyde; C011350:sedridine