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

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Abstract

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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Additional information

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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Keywords

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