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Synthesis of nitrogen-containing drimane sesquiterpenoids from 11-dihomodrim-8(9)-en-12-one

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Products from the reaction of 11-dihomodriman-8α-ol-12-one with several reagents such as MeSO3SiMe3, CF3SO3SiMe3, Sc(CF3SO3)3, conc. H2SO4 in EtOH (30% solution), and Amberlist-15 ion-exchange resin were studied. 11-Dihomodrim-8(9)-en-12-one and its oxime were synthesized. The reaction of its oxime with H3PO4 (86%) or CF3CO2H produced (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydro-1H-naphtho [1,2-e]-3-methyl-4,5-dihydro-[1,2,6]-oxazine; with p-TsCl in Py, (1S,2S,4aS,8aS)-2,5,5,8a-tetramethyldecahydro-1H-naphtho[1,2-d]-2-methylpyrroline-N-oxide; and with PCl5 in Et2O, 11-acetylaminodrim-8(9)-ene and 11-methylaminooxodrim-8(9)-ene.

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Authors and Affiliations

  1. Institute of Chemistry, Academy of Sciences of the Republic of Moldova, Republic of Moldova, MD-2028, Kishinev

    K. I. Kuchkova, A. N. Aryku, A. N. Barba & P. F. Vlad

  2. Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw, Poland

    Ya. Lipkovskii

  3. Institute of Applied Physics, Academy of Sciences of Moldova, ul. Akademiei, 5, MD-2028, Kishinev, Republic of Moldova

    Yu. A. Simonov & V. Kh. Kravtsov

Authors
  1. K. I. Kuchkova
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  2. A. N. Aryku
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  3. A. N. Barba
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  4. P. F. Vlad
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  5. Ya. Lipkovskii
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  6. Yu. A. Simonov
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  7. V. Kh. Kravtsov
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Corresponding author

Correspondence to P. F. Vlad.

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Deceased (Yu. A. Simonov)

Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 205–210, March–April, 2011.

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Kuchkova, K.I., Aryku, A.N., Barba, A.N. et al. Synthesis of nitrogen-containing drimane sesquiterpenoids from 11-dihomodrim-8(9)-en-12-one. Chem Nat Compd 47, 223–228 (2011). https://doi.org/10.1007/s10600-011-9888-2

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  • DOI: https://doi.org/10.1007/s10600-011-9888-2

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