Die absolute Konfiguration von Macrolin, einem Abbauproduct des Alkaloides Villalstonin

Article abstract of DOI:10.1002/hlca.19810640112

The absolute configuration of macroline (1), a degradation product of villalstonine (2), was determined.The chemical degradation of 1 gave a mixture of (-)-(20S)-20,21-hihydro-19-desoxo-macroline (9) and (-)-(20R)-20,21-dihydro-19-desoxo-macroline (10), which was related to the degradation products 9 of (+)-ajmaline (3) and 10 of (+)-isoajmaline (4) of known absolute configuration.Together with the complete relative stereochemistry of 2 the absolute configuration of 2 and of the second moiety of 2, (+)-pleiocarpamine (20), could be derived.Since the absolute configuration of the (-)-6,7-dihydroaspidospermidine moiety of (+)-pycnanthinine has been known already <15>, the structure by Gorman et al. <17> represents the absolute configuration of (+)-pycnanthinine.