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Synthesis of stereoisomeric 7,7,10a-trimethyl-trans-perhydronaphtho[2,1-c]pyrans and 6,6,9a-trimethyl-trans-perhydronaphtho[2,1-b]furans

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Four diastereomeric [with respect to C(4) and C(10)] 7,7,10a-trimethyl-trans-perhydronaphtho[2,1-c]pyrans were synthesized by dehydration of the corresponding 5,5,8a-trimethyl-1-(2-hydroxyethyl)-2-hydroxymethyl-trans-decalins. (1R,2S,8aS)-5,5,8a-Trimethyl-1-(2-hydroxyethyl)-2-hydroxy-trans-perhydronaphthalene, which is dehydrated to give a mixture of epimeric [with respect to C(3a)] (9aS,9bR)-6,6,9a-trimethyl-trans-perhydronaphtho[2,1-b]furans, was obtained from (1R,8aS)-5,5,8a-trimethyl-1-(2-hydroxyethyl)-2-methylene-trans-perhydronaphthalene, All of the synthesized oxide compounds have an intense ambergris odor.

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Literature cited

  1. P. F. Vlad and N. D. Ungur, Khim. Geterotsikl. Soedin., No. 3, 309 (1983).

    Google Scholar 

  2. P. F. Vlad, G. A. Dragalina, and M. N. Koltsa, Zh. Obshch. Khim., 47, 943 (1977).

    Google Scholar 

  3. P. F. Vlad, N. D. Ungur, and M. N. Koltsa, Zh. Obshch. Khim., 48, 1949 (1978).

    Google Scholar 

  4. P. F. Vlad, M. N. Koltsa, and G. A. Dragalina, USSR Inventor's Certificate No. 529166; Byull. Izobret., No. 35, 59 (1976).

  5. G. Ohloff, W. Geersch, K. H. Schulte-Ette, and C. Vial, Helv. Chim. Acta, 59, 1140 (1976).

    Google Scholar 

  6. P. F. Vlad, Kh. Sh. Khariton, and M. N. Koltsa, Khim. Prir. Soedin., No. 4, 449 (1978).

    Google Scholar 

  7. C. R. Enzell and R. Ryhage, Ark. Kem., 23, 367 (1965).

    Google Scholar 

  8. G. Ohloff, Gustation and Olfaction, Academic Press, New York-London (1971).

    Google Scholar 

  9. T. Norin and L. Westfelt, Acta Chem. Scand., 17, 1828 (1963).

    Google Scholar 

  10. W. C. Still, M. Kahn, and A. Mitra, J. Org. Chem., 43, 2923 (1978).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry, Academy of Sciences of the Moldavian SSR, 277028, Kishinev

    P. F. Vlad, M. N. Koltsa, N. D. Ungur, G. A. Dragalina & T. E. Panasyuk

  2. T. G. Shevchenko State Pedagogical Institute, Tiraspol

    P. F. Vlad, M. N. Koltsa, N. D. Ungur, G. A. Dragalina & T. E. Panasyuk

Authors
  1. P. F. Vlad
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  2. M. N. Koltsa
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  3. N. D. Ungur
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  4. G. A. Dragalina
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  5. T. E. Panasyuk
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 315–321, March, 1983.

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Vlad, P.F., Koltsa, M.N., Ungur, N.D. et al. Synthesis of stereoisomeric 7,7,10a-trimethyl-trans-perhydronaphtho[2,1-c]pyrans and 6,6,9a-trimethyl-trans-perhydronaphtho[2,1-b]furans. Chem Heterocycl Compd 19, 253–258 (1983). https://doi.org/10.1007/BF00513254

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  • DOI: https://doi.org/10.1007/BF00513254

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