The phenylquinolizidines of the seedlings of Heimia salicifolia.

Abstract

Two isomeric 2-hydroxy-4-(3-hydroxy-4-methoxyphenyl)quinolizidines (3 and 9a), differing in the configuration of the bridgehead carbon, have been isolated from 5 to 10-day-old seedlings of Heimia salicifolia. The phenylquinolizidol with the cis ring juncture is shown to exist, in solution, as an equilibrium of conformers. 2-Keto-4-(3-hydroxy-4-methoxyphenyl)quinolizidine (5) has been isolated from the seedlings by radioactive dilution.