Synthesis of 12-amino-11-dihomodrimane Sesquiterpenoids from Norambreinolide

Abstract

A series of dihomodrimane sesquiterpenoids containing an NH 2 group were synthesized. 11-Dihomodriman-8D-ol-12-one and its dehydration products, ketones with double bonds in the C 7 -C 8 and C 8 -C 9 positions, were prepared from commercially available norambreinolide. The oximes of the ketones were reduced by LiAlH 4 to the corresponding amines.

Synthesis of New Drimane and Homodrimane Lactams by Beckmann Rearrangement of Some Ketoximes

“…In a search for new biologically active compounds and in continuation of our group's investigations of obtaining nitrogen-containing sesquiterpenoids [2][3][4][5], in the present paper the synthesis of new drimane and homodrimane lactams by the Beckmann rearrangement of some ketoximes is described.…”

“…Therefore, it has been expected that the major product of the Beckmann rearrangement of oxime 10 would be amide 7. However, in the case of oxime 10, amide 9 is obtained as a result of the migration of CH 3 …”

Synthesis of New Nitrogen-Containing Drimane and Homodrimane Sesquiterpenoids from Sclareolide

“…Later, 11-aminodrim-7-ene 3 was synthesized from drimenol 4 [4][5][6]. Recently, 12-amino-11-dihomodrim-8-ol 5 and products 6 and 7 of its dehydration have been synthesized from sclareolide 8 [7] and 13-amino-14,15-dinorlabd-8(9)-ene 9 from sclareol 10 [8] (Figure 1).…”