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

Products from the reaction of 11-dihomodriman-8 α -ol-12-one with several reagents such as MeSO 3 SiMe 3 , CF 3 SO 3 SiMe 3 , Sc(CF 3 SO 3 ) 3 , conc. H 2 SO 4 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 r...

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Bibliographic Details
Published in:Chemistry of natural compounds 2011-05, Vol.47 (2), p.223-228
Main Authors: Kuchkova, K. I., Aryku, A. N., Barba, A. N., Vlad, P. F., Lipkovskii, Ya, Simonov, Yu. A., Kravtsov, V. Kh
Format: Article
Language:English
Subjects:
Medicine
Organic Chemistry
Pharmacy
Plant Sciences
Sesquiterpenes
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Summary:Products from the reaction of 11-dihomodriman-8 α -ol-12-one with several reagents such as MeSO 3 SiMe 3 , CF 3 SO 3 SiMe 3 , Sc(CF 3 SO 3 ) 3 , conc. H 2 SO 4 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 H 3 PO 4 (86%) or CF 3 CO 2 H produced (1 S ,2 S ,4a S ,8a S )-2,5,5,8a-tetramethyldecahydro-1 H -naphtho [1,2- e ]-3-methyl-4,5-dihydro-[1,2,6]-oxazine; with p -TsCl in Py, (1 S ,2 S ,4a S ,8a S )-2,5,5,8a-tetramethyldecahydro-1 H -naphtho[1,2- d ]-2-methylpyrroline- N -oxide; and with PCl 5 in Et 2 O, 11-acetylaminodrim-8(9)-ene and 11-methylaminooxodrim-8(9)-ene.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-011-9888-2