Die absolute Konfiguration von Macrolin, einem Abbauprodukt des Alkaloides Villalstonin 179. Mitteilung über organische Naturstoffe

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Abstract
The Absolute Configuration of Macroline, a Degradation Product of the Alkaloid VillalstonineThe absolute configuration of macroline (1), a degradration product of villalstonine (2), was determined. The chemical degradation of 1 gave a mixture of (–)‐(20S)‐20,21‐dihydro‐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.