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

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

“…Oximes 22 and 23 have been obtained earlier [10] from the commercially available norambreinolide 24 according to the procedure [11].…”

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

“…Drimene oxime 13 was prepared by the reaction of drim-8-en-7-one 12 with hydroxylamine hydrochloride in a mixture of ethanol:pyridine (1:1) in 98% yield as in [11]. The desired product, 7-amino-drim-8(9)-ene 14, was obtained in 51% yield by refl uxing oxime 13 with LiAlH 4 in anhydrous THF as in [8].…”

“…The structure of compound 14 was confi rmed by IR, 1 H, and 13 C NMR data. In another case, ketoester 11 was treated with hydroxylamine hydrochloride in a mixture of ethanol:pyridine (1:1), giving ester oxime 15 described in [11], which was subsequently saponifi cated with KOH in methanol into the oxime 16 in 95% yield.…”

“…The organic layer was washed with 10% HCl (10 mL), NaHCO 3 solution (10 mL) and water (15 mL), dried over anhydrous Na 2 SO 4 and fi ltered. The solvent removal under a reduced pressure as in [11] led to oximes 13 (0.59 g, 98%) or 15 (0.72 g, 98%), as white solids. …”

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

“…In continuation of our research on the synthesis of N-containing drimane and homodrimane sesquiterpenoids [6][7][8][9], herein we report the preparation of 12-amino-11-dihomodrim-8D-ol (5) and its dehydrated analogs 6 and 7 (Scheme 1).…”