Synthesis of nitrogen-containing drimane sesquiterpenoids from 11-dihomodrim-8(9)-en-12-one |
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Authors: | K I Kuchkova A N Aryku A N Barba P F Vlad Ya Lipkovskii Yu A Simonov V Kh Kravtsov |
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Institution: | 1.Institute of Chemistry,Academy of Sciences of the Republic of Moldova,Kishinev,Republic of Moldova;2.Institute of Physical Chemistry,Polish Academy of Sciences,Warsaw,Poland;3.Institute of Applied Physics,Academy of Sciences of Moldova,Kishinev,Republic of Moldova |
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Abstract: | 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-naphtho1,2-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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