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.