title: Asymmetric synthesis of (-)-indolizidines 167B and 209D based on stereocontrolled allylation of a chiral tricyclic N-acyl-N,O-acetal.
abstract: [reaction: see text] The tricyclic N-acyl-N,O-acetal incorporating (S)-2-(1-aminoethyl)phenol as a chiral auxiliary underwent TiCl4-mediated allylation to give the chiral (5S)-allylpyrrolidinone with retention of configuration in high yield and diastereoselectivity. On the bases of this methodology, the asymmetric syntheses of the dendrobatid alkaloids (-)-indolizidines 167B and 209D were achieved.
authors.affiliation: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Hachioji, Japan.
authors.forename: N
authors.initials: N
authors.lastname: Yamazaki
authors.forename: T
authors.initials: T
authors.lastname: Ito
authors.forename: C
authors.initials: C
authors.lastname: Kibayashi
mesh_terms: D000080:Acetals / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D007211:Indoles