Chemistry of Natural Compounds

, Volume 5, Issue 6, pp 488–493 | Cite as

Olivomycin and related antibiotics

XXI. Periodate oxidation of olivin
  • G. P Bakhaeva
  • Yu. A. Berlin
  • M. N. Kolosov
  • O. A. Chuprunova
Article
  • 21 Downloads

Conclusions

The oxidation of olivin (I) by periodate takes place by three alternative routes, two of which include the stage of the intermediate formation of a cyclic semiacetal with the participation of the 2-OH hydroxyl and a 3′-CO or 2′-CO carbonyl group. As a result of this, the oxidative degradation of the dihydroxyketonic grouping of the side chain to form a carboxyl group is accompanied by intramolecular O2-formylation and lactonization, giving as the main product 2-O-formylolivinic acid (IV), together with olivinic acid (VII), and its lactone (XX).

Keywords

Periodate Diazomethane Periodate Oxidation Sodium Periodate Ketol 

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References

  1. 1.
    Yu. A. Berlin, M. N. Kolosov, I. V. Vasina, and I. V. Yartseva, Chem. Commun., 762, 1968.Google Scholar
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    G. P. Bakhaeva, Yu. A. Berlin, E. F. Boldyreva, O. A. Chuprunova, M. N. Kolosov, V. S. Soifer, T. E. Vasilyeva, and I. V. Yartseva, Tetrah. Let., 3595, 1968.Google Scholar
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    Yu.A. Berlin, I.V. Vasina, M.N. Kolosov, G.Yu. Pek, L. A. Piotrovich, and O.A. Chuprunova, KhPS [Chemistry of Natural Compounds],5, 304, 1969.Google Scholar
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    W. Mackie and A. S. Perlin, Can. J. Chem. 43, 2645, 1965.CrossRefGoogle Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • G. P Bakhaeva
    • 1
  • Yu. A. Berlin
    • 1
  • M. N. Kolosov
    • 1
  • O. A. Chuprunova
    • 1
  1. 1.Institute of the Chemistry of Natural Compounds, AS USSRUSSR

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