Chemistry of Natural Compounds

, Volume 17, Issue 5, pp 442–446 | Cite as

NMR investigation of alkaloids

II. Determination of the configurations of the C17 and C2 asymmetric centers in indoline alkaloids of the ajmaline type by the double proton resonance method
  • M. R. Yagudaev
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Abstract

By the method of double proton resonance, in the alkaloids of the ajmaline type, ajmaline, majoridine, herbamine, quebrachidine (vincarine), vincamajine, and vincamedine a long-range stereospecific interaction through four σ-bonds between the H and H17α protons of about 1 Hz has been found and in compounds with C2-βH and C17-αH (ajmaline, majoridine), the H2β and H17α protons exhibit a NOE of the order of 10%. These facts can be used successfully in determining the orientation of the hydrogen atoms and the corresponding configurations of C17 and C2 asymmetric centers in such systems.

Keywords

Alkaloid Dihedral Angle Spin Coupling Nuclear Overhauser Effect Asymmetric Center 

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Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • M. R. Yagudaev

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