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Modified synthesis of methyl (1R,2R,3E,5R)-3-(hydroxyimino)-5-methyl-2-(1-methylethyl)-cyclohexanecarboxylate from (R)-4-menthen-3-one

Author:
Ishmuratov, G. Yu., Bannova, A. V., Latypova, E. R., Muslukhov, R. R., Smol′nikov, A. A., Talipov, R. F.
Source:
Chemistry of natural compounds 2012 v.48 no.5 pp. 789-790
ISSN:
0009-3130
Subject:
catalysts, chlorides, ethers, monoterpenoids, redox reactions, synthesis
Abstract:
A modified stereospecific synthesis of potentially biologically and pharmacologically active methyl (1R,2R,3E,5R)-3-(hydroxyimino)-5-methyl-2-(1-methylethyl)cyclohexanecarboxylate from (R)-4-menthen-3-one was developed using sequential 1,4-conjugate addition of Norman reagent catalyzed by CuI–BF₃[Symbol: see text]Et₂O–CuCl₂ and ozonolysis–reduction of the intermediate (R,R,R)-vinylmenthone by hydroxylamine hydrochloridein MeOH.
Agid:
462285