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Prilezhaev dihydroxylation of (R)-octadec-9Z-en-7-0l

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Chemistry of Natural Compounds Aims and scope

Formation of new asymmetric centers with primarily the (S)-configuration was induced by the optically active center of (R)-octadec-9Z-en-7-ol upon Prilezhaev dihydroxylation. This was proved by cyclization of a 1,3-glycol system (de 26%) into the corresponding 1,3-dioxane stereoisomers.

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References

  1. R. R. Muslukhov, A. Kh. Shayakhmetova, M. P. Yakovleva, O. V. Shitikova, G. Yu. Ishmuratov, and G. A. Tolstikov, Zh. Org. Khim., 44, 1145 (2008).

    Google Scholar 

  2. G. Yu. Ishmuratov, R. Ya. Kharisov, A. Kh. Shayakhmetova, L. P. Botsman, O. V. Shitikova, and G. A. Tolstikov, Khim. Prir. Soedin., 529 (2005).

  3. J. J. Li, Name Reactions: A Collection of Detailed Reaction Mechanisms, Springer, Berlin, New York, 2006.

    Google Scholar 

  4. N. M. Davletbakova, N. Z. Baibulatova, V. A. Dokichev, R. R. Muslukhov, S. G. Yunusova, and M. S. Yunusov, Zh. Org. Khi., 37, 1287 (2001).

    Google Scholar 

  5. D. Barton and W. D. Ollis (eds.), Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds, Vol. 2, Nitrogen Compounds, Carboxylic Acids, Phosphorus Compounds, Pergamon Press, Oxford, New York, 1979.

  6. M. Sharma and R. K. Brown, Can. J. Chem., 44, 2825 (1966).

    Article  CAS  Google Scholar 

  7. N. K. Kochetkov, A. F. Sviridov, M. S. Ermolenko, and O. S. Chizhov, Carbohydrates in the Synthesis of Natural Compounds [in Russian], Nauka, Moscow, 1984.

    Google Scholar 

  8. H. Kuzuhara, H. Ohrui, and S. Emoto, Agric. Biol. Chem., 35, 8 (1971).

    CAS  Google Scholar 

  9. E. Breitmaier and W. Voelter, 13 C NMR-Spectroscopy, Verlag Chem, Weinheim, Bergstr., 1974.

  10. V. V. Klochkov, Sh. K. Latypov, A. N. Rakhmatullin, R. M. Vafina, E. N. Klimovitskii, and A. V. Aganov, Zh. Obshch. Khim., 68, 140 (1998).

    Google Scholar 

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Acknowledgment

The work was supported financially by RFBR Grant No. 09-03-00831.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Russian Federation, 450054, Ufa, prosp. Oktyabrya, 71

    R. R. Muslukhov, A. Kh. Shayakhmetova, O. O. Shakhanova, M. P. Yakovleva, G. Yu. Ishmuratov & A. G. Tolstikov

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  1. R. R. Muslukhov
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  2. A. Kh. Shayakhmetova
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  3. O. O. Shakhanova
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  4. M. P. Yakovleva
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  5. G. Yu. Ishmuratov
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  6. A. G. Tolstikov
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Corresponding author

Correspondence to M. P. Yakovleva.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 537–539, September–October, 2009.

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Muslukhov, R.R., Shayakhmetova, A.K., Shakhanova, O.O. et al. Prilezhaev dihydroxylation of (R)-octadec-9Z-en-7-0l. Chem Nat Compd 45, 637–640 (2009). https://doi.org/10.1007/s10600-009-9441-8

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  • DOI: https://doi.org/10.1007/s10600-009-9441-8

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