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1. (R)-n-menth-4-en-3-one and its Derivatives in Reactions with N-containing Reagents

Author:
Muslukhov, R. R.,   et al.   ; Ishmuratov, G. Yu.; Tukhvatshin, V. S.; Yakovleva, M. P.; Allagulova, A. V.; Talipova, G. R.;     Show all 6 Authors
Source:
Chemistry of natural compounds 2014 v.50 no.2 pp. 272-275
ISSN:
0009-3130
Subject:
chemical reactions; synthesis
Abstract:
... The reactions of (R)-n-menth-4-en-3-one and its derivatives with N-containing reagents were studied. New menthane-type acetamides were synthesized. ...
DOI:
10.1007/s10600-014-0929-5

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

Author:
Muslukhov, R. R.,   et al.   ; Ishmuratov, G. Yu.; Bannova, A. V.; Latypova, E. R.; Smol′nikov, A. A.; Talipov, R. F.;     Show all 6 Authors
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 hydr ...
DOI:
10.1007/s10600-012-0383-1

3. Synthesis of optically active macrolides with hydrazide fragments from tetrahydropyran and L-(+)-tartaric acid derivatives

Author:
Muslukhov, R. R.,   et al.   ; Ishmuratov, G. Yu.; Yakovleva, M. P.; Mingaleeva, G. R.; Shutova, M. A.; Vyrypaev, E. M.; Tolstikov, A. G.;     Show all 7 Authors
Source:
Chemistry of natural compounds 2013 v.49 no.4 pp. 691-693
ISSN:
0009-3130
Subject:
acids; hydrazides; macrolides; synthesis
Abstract:
... The synthesis of two potentially useful optically active 23- and 30-membered macrolides containing a 1,2-diol system and dihydrazide fragments was developed starting from tetrahydropyran. It was based on [1+1]-condensation of 7-oxooctyl-7-oxooctanoate and bis(7-oxooctyl)hexanedioate with L-(+)-tartaric acid hydrazide. ...
DOI:
10.1007/s10600-013-0708-8

4. Prilezhaev dihydroxylation of (R)-octadec-9Z-en-7-0l

Author:
Muslukhov, R. R.,   et al.   ; Shayakhmetova, A. Kh.; Shakhanova, O. O.; Yakovleva, M. P.; Ishmuratov, G. Yu.; Tolstikov, A. G.;     Show all 6 Authors
Source:
Chemistry of natural compounds 2009 v.45 no.5 pp. 637-640
ISSN:
0009-3130
Subject:
dioxane; glycols; hydroxylation; stereoisomers; synthesis
Abstract:
... Formation of new asymmetric centers with primarily the (S)-configuration was induced by the optically active center of (R)-octadec-9Z-en-7-ol upon Prilezhaev dihydroxylation. This was proved by cyclization of a 1,3-glycol system (de 26%) into the corresponding 1,3-dioxane stereoisomers. ...
DOI:
10.1007/s10600-009-9441-8

5. Synthesis of symmetric macrocyclic diesterdihyrazides using successive [2+1]- and [1+1]-condensations

Author:
Muslukhov, R. R.,   et al.   ; Ishmuratov, G. Yu.; Mingaleeva, G. R.; Yakovleva, M. P.; Vyrypaev, E. M.; Ivanov, S. P.; Tolstikov, A. G.;     Show all 7 Authors
Source:
Chemistry of natural compounds 2010 v.46 no.1 pp. 10-14
ISSN:
0009-3130
Subject:
chlorides; hydrazides; petrochemicals; synthesis
Abstract:
... Potentially useful symmetric macrocyclic diesterdihydrazides were synthesized efficiently from available petrochemical products (tetrahydropyran and 4-methyltetrahydropyran) using successive [2+1]-condensation of 8-hydroxyoctan-2-one and its 6-methyl derivative with glutaric and adipic chlorides and [1+1]-condensation of the intermediate diketodiesters with glutaric dihydrazide. ...
DOI:
10.1007/s10600-010-9513-9

6. Synthesis of the Promising Chiral Synthon Isopropyl-4R-Methyl-6-Iodohexanoate from L-(-)-Menthol

Author:
Muslukhov, R. R.,   et al.   ; Ishmuratov, G. Yu.; Yakovleva, M. P.; Ganieva, V. A.; Tolstikov, G. A.;     Show all 5 Authors
Source:
Chemistry of natural compounds 2005 v.41 no.1 pp. 41-44
ISSN:
0009-3130
Subject:
chemical derivatives; menthol; synthesis
Abstract:
... A synthesis of the promising optically pure synthon isopropyl-4R-methyl-6-iodohexanoate based on ozonolytic transformation of the product of regiospecific dehydratation of L-(-)-menthol, (R)-p-menth-3-ene, into 2,6R-dimethyl-8-hydroxyoctan-3-one was proposed. ...
DOI:
10.1007/s10600-005-0070-6

7. Synthesis of Optically Pure 3R-methylcyclopentan-1-one from L-(-)-menthol

Author:
Muslukhov, R. R.,   et al.   ; Ishmuratov, G. Yu.; Yakovleva, M. P.; Ganieva, V. A.; Gareeva, G. R.; Tolstikov, G. A.;     Show all 6 Authors
Source:
Chemistry of natural compounds 2005 v.41 no.5 pp. 549-551
ISSN:
0009-3130
Subject:
chemical reactions; menthol; synthesis
Abstract:
... Synthesis of optically pure 3R-methylcyclopentan-1-one using in the key step Dieckmann cyclization of diisopropyl 3R-methylhexan-1,6-dioate, which is accessible from L-(-)-menthol, was proposed. ...
DOI:
10.1007/s10600-005-0203-y