The Total Synthesis of Ipalbidine and Ipalbine
Wick, A.E., Bartlett, P.A., and David Dolphin
Helv. Chim. Acta,
The hexahydroindolizine alkaloid ipalbidine and its β-D-glucoside ipalbine were synthesized from 2-methoxypyrroline and AcCH2CO2Me via Me acetyl-2-pyrrolidineacetate, which was condensed with p-MeOC6H4CH2-COCl to give Me 1,2,3,5-tetrahydro-6-(4-methoxyphenyl)-7-methyl-5-oxoindolizine-8-carboxylate. Spectral data indicate that natural ipalbidine is a racemate.