Asymmetric synthesis of (-)-indolizidines 167B and 209D based on stereocontrolled allylation of a chiral tricyclic N-acyl-N,O-acetal.
[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.
Yamazaki
N
N
School of Pharmacy, Tokyo University of Pharmacy and Life Science, Hachioji, Japan.
Ito
T
T
Kibayashi
C
C
D000080:Acetals / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000080:Acetals; D007211:Indoles