Anomalous hydroalumination of methyl nopol ether with a LiAlH4-3AlBr3 system

Hydroalumination of methyl nopol ether with a LiAlH₄-3AlBr₃ system is accompanied by a skeleton rearrangement and gives 6-dibromoalumo-7-methoxymethyl-2-menthene. Further hydroalumination affords a mixture of 2,6- and 2,5-bis(dibromoalumo)-7-(methoxymethyl)menthanes in 8020 ratio. Hydrolysis and oxidation of these organoaluminum compounds were carried out.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 506–510, March, 1994.     

Synthesis and asymmetric oxidation of thioglycosides derived from neomenthanethiol and α-d-galactose

6-Deoxy-6-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexylsulfanyl]-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose was synthesized in 94% yield from 1,2 : 3,4-di-O-isopropylidene-α-d-galactopyranose and neomenthanethiol, and its oxidation gave the corresponding diastereoisomeric sulfoxides in up to 84% yield and de values of up to 52%. The isopropylidene protective groups were removed from the sulfide and sulfoxides by treatment with trifluoroacetic acid in chloroform.     

Synthesis and evaluation of the antioxidant properties for some novel aminomethyl derivatives of 2,6-diisobornylphenol bearing a pinane moiety

Some new derivatives based on 2,6-diisobornylphenol and containing amine moieties of the pinane structure at the para-position relative to the phenolic hydroxy group were synthesized. The antioxidant properties of the obtained compounds were estimated using various in vitro models. The introduction of diamine moiety into a starting molecule led to a significant increase in the radical scavenging activity and the ability to chelate Fe²⁺ ions.

     

Resolution of racemic 2-isobornyl-4-methylphenol into enantiomers

Resolution of racemic 2-isobornyl-4-methylphenol into enantiomers was performed following its transformation into diastereomers by the reaction with (1S)-camphanoyl chloride.     

Asymmetrically substituted tetra(meso-aryl)porphyrins bearing peripheral 2,6-diisobornylphenol and 2,6-di-tert-butylphenol moieties

Russian Chemical Bulletin - Asymmetrically substituted tetra(meso-aryl)porphyrins bearing peripheral diisobornyl- phenol and di-tert-butylphenol moieties were synthesized by a mixed aldehyde...     

Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone

Carane-derived β-amino alcohols with amino and hydroxy groups at positions 3 and 4 differing in their mutual arrangement and configuration were synthesized. Their application as organocatalysts in the asymmetric aldol reaction of isatin with acetone allowed one to obtain adducts with up to 84% enantiomeric excess.     

Composition and properties of the reaction products of p-cresol with camphene

Russian Chemical Bulletin - The products of the reaction between p-cresol and camphene were isolated and characterized. Their antiradical activity and toxicity were studied. The pharmacological...     

Design,synthesis and evaluation of the antioxidant and neuroprotective properties of alkyl- and terpenylphenolchlorin conjugates

The new amide conjugates were synthesized from methyl pheophorbide a and its carboxyl derivatives by reactions with aminomethyl derivatives of 2,4-dimethylphenol, 2-isocamphyl-4- methylphenol, 2-bornyl-4-methylphenol, and 2-isobornyl-4-methylphenol. The antioxidant activity of some conjugates was established by investigation of their ability to inhibit the accumulation of secondary products of lipid peroxidation in a brain of laboratory mice in vitro. The neuroprotective properties of porphyrin and terpenylphenol conjugates have been studied on the model of H₂O₂-induced oxidative stress in SH-SY5Y cells (neuroblastoma).

     

Synthesis of Chiral 3,4-Dihydropyrimidin-2(1H)-one Derivatives and Their Stereoselective Chlorination with Chlorine Dioxide

Russian Journal of Organic Chemistry - Optically active derivatives of 3,4-dihydropyrimidin-2(1H)-one have been synthesized on the basis of myrtenal and methyl...