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Synthesis of nitrogen-containing drimane sesquiterpenoids from 11-dihomodrim-8(9)-en-12-one
Authors:K I Kuchkova  A N Aryku  A N Barba  P F Vlad  Ya Lipkovskii  Yu A Simonov  V Kh Kravtsov
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
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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