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Über Muscarin

Synthese eines Gemischs von Muscarin und seinen stereoisomeren Formen

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Summary

A recent investigation ofKögl, Salemink, Schouten andJellinek established the constitution of muscarin as the quaternary trimethyl-ammonium salt of 2-methyl-3-hydroxy-5- (amino - methyl) - tetrahydrofuran. Moreover the X-ray analysis elucidated the complete stereochemical configuration of the alkaloid.

There are various possibilities for a synthetic approach. The present communication gives a preliminary description of a synthesis which started fromα-acetyl-δ-chloro-γ-valerolactone, leading to a mixture of muscarin and its stereochemical isomers. The synthetic product gives the same RF-value and a very similar infrared spectrum. The pharmacological activity on the frog heart is about one third of that of the natural alkaloid.

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References

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Authors and Affiliations

  1. Organisch-chemisches Laboratorium der Rijksuniversiteit Utrecht, Holland

    F. Kögl, H. C. Cox & C. A. Salemink

Authors
  1. F. Kögl
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  2. H. C. Cox
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  3. C. A. Salemink
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Additional information

4. Mitteilung über Muscarin.

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Kögl, F., Cox, H.C. & Salemink, C.A. Über Muscarin. Experientia 13, 137–138 (1957). https://doi.org/10.1007/BF02158130

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  • DOI: https://doi.org/10.1007/BF02158130

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