Über die basischen Inhaltsstoffe des Fliegenpilzes: XI. Mitteilung über das Muscaridin und Seine Stereoisomeren†‡

This communication contains a description of the isolation of muscaridine from Amanita muscaria L. The constitution of muscaridin is established as erythro-4,5-dihydroxy-n-hexyltrimethylammoniumchloride. The synthesis, starting from 2,3-dihydropyran, leads to racemic muscaridine. The resolution of racemic muscaridine succeeded with di-p. toluyl-L- tartaric acid and with di-p. toluyl-D-tartaric acid. The synthetic product has the same RF-value, a fully identical infrared spectrum and equal optical rotation as the natural base. The syntheses of threo-4,5-dihydroxy-n-hexyltrimethylammoniumchloride and of 5-hydroxy-n-hexyltrimethylammoniumchloride are described as well.