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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

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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 H6α 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.

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Authors
  1. M. R. Yagudaev
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Additional information

For Communication I, see [1].

Delivered at an All-Union Conference on Modern Advances in High-Resolution NMR spectroscopy, Tashkent, September, 1975 [2].

Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 608–613, September–October, 1981.

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Yagudaev, M.R. NMR investigation of alkaloids. Chem Nat Compd 17, 442–446 (1981). https://doi.org/10.1007/BF00565159

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  • DOI: https://doi.org/10.1007/BF00565159

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