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

Products from the reaction of 11-dihomodriman-8α-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 (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 PCl 5 in Et 2 O, 11-acetylaminodrim-8(9)-ene and 11-methylaminooxodrim-8(9)-ene.