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Retro-michael reaction of 28-methoxy-18,19-secolupane-18,19-dione derivatives

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The interactions with KOH in boiling diethyleneglycol of 3β,28-dimethoxy- and 3β-acetoxy-28-methoxy-18,19-secolupane-18,19-diones have been studied. In the first case, 3β-methoxy-19,20,21,22,29,30-hexanor-18,19-seco(17βH)lupan-18-one and the corresponding 18-ol were isolated from the mixture of products, and in the second case 3β-hydroxy-19,20,21,22,29,30-hexanor-18,19-seco(17βH)lupan-18-one — which was also obtained by an analogous reaction from 3β-acetoxy-18,19-secolupan-18,19-dione — and 3β-hydroxy-19,20,21,22,28,29,30-heptanor-18,19-secolupan-18-one. Thus, it has been found that in this case the retro-Michael reaction is accompanied by 28-demethoxylation and partially by 28-demethoxy-methylation.

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Literature cited

  1. 1.

    D. Arigoni, R. Viterbo, M. Dunnenberger, and M. Ruzicka, Helv. Chim. Acta,37, 2306–2322 (1954); Chem. Abstr.,49, 14,692 (1955).

  2. 2.

    D. H. R. Barton, P. de Mayo, and J. C. Orr, J. Chem. Soc., No. 6, 2239–2248 (1958).

  3. 3.

    G. V. Baddeley, T. G. Halsal, and E. R. H. Jones, J. Chem. Soc., No. 3, 1173–1181 (1964).

  4. 4.

    F. R. Aquino Neto, J. M. Trendel, and P. Alberti, Tetrahedron,42, No. 20, 5621–5626 (1986).

  5. 5.

    M. V. Denisenko, L. É. Odinokova, and N. I. Uvarova, Khim. Prir. Soed., No. 5, 655–664 (1989).

  6. 6.

    M. V. Denisenko, L. É. Odinokova, V. A. Denisenko, and N. I. Uvarova, The Chemistry of Natural Low-Molecular-Mass Bioregulators: Abstracts of Lectures at an All-Union Conference, Erevan, October 29–November 12, 1990. Erevan (1990), p. 66.

  7. 7.

    G. V. Baddeley, J. J. Simes, and T. G. Watson, Tetrahedron,26, No. 15, 3799–3784 [sic] (1970).

  8. 8.

    V. Pouzar and A. Vystrčil, Collect. Czech. Chem. Commun.,41, No. 11, 3452–3466 (1976).

  9. 9.

    E. Suokas and T. Hase, Acta Chem. Scand.,B31, No. 7, 633–635 (1977).

  10. 10.

    L. Fieser and M. Fieser, Reagents for Organic Synthesis, Wiley, New York, Vol. I (1967), p. 191.

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Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 210–215, March–April, 1992.

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Odinokova, L.É., Denisenko, M.V., Denisenko, V.A. et al. Retro-michael reaction of 28-methoxy-18,19-secolupane-18,19-dione derivatives. Chem Nat Compd 28, 179–184 (1992). https://doi.org/10.1007/BF00630170

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  • Organic Chemistry
  • Dione
  • Seco
  • Analogous Reaction
  • Diethyleneglycol