Die absolute Konfiguration von Macrolin, einem Abbauprodukt des Alkaloides Villalstonin 179. Mitteilung über organische Naturstoffe
1981; Wiley; Volume: 64; Issue: 1 Linguagem: Inglês
10.1002/hlca.19810640112
ISSN1522-2675
AutoresGisela Neukomm, Erika Kletzhäundler, Manfred Hesse,
Tópico(s)Plant-based Medicinal Research
ResumoThe Absolute Configuration of Macroline, a Degradation Product of the Alkaloid Villalstonine The absolute configuration of macroline (1) , a degradration product of villalstonine (2) , was determined. The chemical degradation of 1 gave a mixture of (–)‐(20 S )‐20,21‐dihydro‐19‐desoxo‐macroline (9) and (–)‐(20 R )‐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.
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