2011
DOI: 10.1007/s10600-011-9888-2
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Synthesis of nitrogen-containing drimane sesquiterpenoids from 11-dihomodrim-8(9)-en-12-one

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Cited by 14 publications
(11 citation statements)
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“…Oximes 22 and 23 have been obtained earlier [10] from the commercially available norambreinolide 24 according to the procedure [11].…”
Section: Resultsmentioning
confidence: 99%
“…Oximes 22 and 23 have been obtained earlier [10] from the commercially available norambreinolide 24 according to the procedure [11].…”
Section: Resultsmentioning
confidence: 99%
“…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].…”
Section: Resultsmentioning
confidence: 99%
“…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.…”
Section: Resultsmentioning
confidence: 99%
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“…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).…”
mentioning
confidence: 99%