F. A. Gimalova

Disaccharide blocks for analogs of OSW-1

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.

New monomers for fullerene-containing polymers

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.

Esters of dichloroacetic acid in the synthesis of fullerene C60 functionalized methane derivatives

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

Bis(Allyloxycarbonyl)methano derivatives of fullerene C60

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.

Reaction of 5-Allyl-2,3,5-trichloro-4,4-dimethoxycyclopent-2-en-1-one with amino acids

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.

Science-intensive utilization of environmentally harmful polychlorocarbons. Synthesis of biologically active cyclopentanoids from hexachlorocyclopentadiene

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

Reaction of hexachlorobutadiene with sodium methoxide

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.

Chiral cyclohexene block from R-(−)-carvone

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.

New disaccharide blocks for OSW-1 and its analogs

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.

Oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl) methanol with pyridinium chlorochromate

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.