F. A. Gimalova

L. S. Khasanova; F. A. Gimalova; S. A. Torosyan; A. A. Fatykhov; M. S. Miftakhov

The acetalization of phenyl 1-thio-α-L-arabinopyranoside with 2,3-butanedione in the medium of MeOH-CH(OMe)3-CSA proceeded with the prevailing formation of the corresponding 3,4-bisacetal that further was converted in compounds, which were regio- and stereoisomers of disaccharide block of OSW-1.

S. A. Torosyan; Yu. N. Biglova; V. V. Mikheev; F. A. Gimalova; Akhat G. Mustafin; M. S. Miftakhov

By reaction of 2-(acryloyloxyethyl) and (undecen-10-en-1-yl) methylmalonates with fullerene C60 in the system toluene-CBr4-DBU, and also by reaction of 2-(2,2-dichloroacetoxy)ethyl acrylate with C60 in the system toluene-DBU the corresponding products of fullerene monocyclopropanation were synthesized.

S. A. Torosyan; F. A. Gimalova; Yu. N. Biglova; V. V. Mikheev; M. S. Miftakhov

X C It is well known that carbanions generated in situ from α-halomalonic esters cleanly react with fullerene С60 giving cyclopropane derivatives. This is a general approach that has been performed on versatile derivatives of malonic esters [1–4], Meldrum’s acid [5], and the other СН-acids [6]. The indispensable condition of the reaction to proceed is the possibility to generate from the reagent carbanion А possessing a halomethine function that adds to the electron-defi cient double bond of С60 providing the secondary carbanion B which via the intramolecular cyclization gives cyclopropanes C (Scheme 1). In this study we tested allyl dichloroacetate (I) as a new cyclopropanation agent for С60. As seen from the structure, the methane proton of compound I is strongly activated, it should be easily converted into a carbanion, and for the intramolecular cyclization the presence is feasible of a good leaving group (Cl–). In total this reaction rout should provide cyclopropanes D. The experimental test showed that in the reaction of about equimolar

S. A. Torosyan; F. A. Gimalova; V. V. Mikheev; A. A. Fatykhov; Yu. N. Biglova; M. S. Miftakhov

Mono-, bis-, tris-, tetrakis-, and hexakis-substituted cyclopropanation products of fullerene C60 with diallyl malonate were synthesized according to Bingel-Hirsch. Except for the monocyclopropanation product, all other adducts were isolated as mixtures of regioisomers.

F. A. Gimalova; V. A. Egorov; S. A. Torosyan; M. S. Miftakhov

Abstract5-Allyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one reacts with L-proline and L-methionine methyl esters to give diastereoisomeric mixtures of the corresponding chlorine replacement products at C3.

G. A. Tolstikov; S. A. Ismailov; F. A. Gimalova; N. A. Ivanova; M. S. Miftakhov

The review summarizes the research results and application aspects of the original series of trichlorocyclopentenones synthesized from hexachlorocyclopentadiene.

V. A. Egorov; F. A. Gimalova; L. S. Khasanova; M. S. Miftakhov

Hexachlorobutadiene reacts with MeONa in refluxing methanol to give (Z)-4,4-dimethoxy2-oxobut-3-enoic acid and 2,4,4-trichloro-1,1,1,3-tetramethoxybut-2-ene, which were converted to methyl (Z)-4,4-dimethoxy-2-oxobut-3-enoate and methyl (Z)-2,4,4-trichloro-3methoxybut-2-enoate upon treatment with CH2N2 and acid hydrolysis, respectively.

F. A. Gimalova; G. M. Khalikova; S. A. Torosyan; D. Z. Akhmetshina; M. S. Miftakhov

The oxidation with SeO2 of a methyl group linked to an sp2-hybridized carbon in the product of the intramolecular iodoetherification of cis-carveol afforded (1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]-oct-3-en-4-carbaldehyde and [(1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]oct-3-en-4-yl]methanol that were oxidized to methyl (1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]oct-3-en-4-carboxylate. The latter by the Zn-promoted opening of the γ-oxide ring was converted into the target chiral block, methyl (4R,6R)-6-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-encarboxylate.

L. S. Khasanova; F. A. Gimalova; Z. R. Valiullina; N. K. Selezneva; R. M. Ganieva; L. V. Spirikhin; M. S. Miftakhov

A new disaccharide block for OSW-1 natural steroidal antitumor agent was described. Regioisomeric 2- and 3-O-p-methoxybenzoyl derivatives of phenyl 1-thio-β-d-xylopyranoside and phenyl 2-O-acetyl-1-thio-β-l-arabinopyranoside derivatives blocked at positions 3 and 4 by R3Si groups were synthesized with a view to use them in the preparation of OSW-1 analogs modified at the disaccharide fragment.

S. A. Torosyan; F. A. Gimalova; R. F. Valeev; M. S. Miftakhov

The oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl)methanol epimeric at the C7 atom resulted in scalemic (5R)-5-acetyl-2-methylcyclohex-2-en-1-one.