D. V. Sudarikov

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

Abstract6-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.

Asymmetric oxidation of hetaryl neomenthyl sulfides

Previously unknown diastereoisomeric sulfoxides were synthesized by asymmetric oxidation of 2-neomenthylsulfanyl-substituted 1H-imidazole, 1-methyl-1H-imidazole, and 1H-benzimidazole.

Functionalized mercaptoacetic and propionic acid amides: synthesis, cyclopalladation features, and catalytic activity of metal complexes

Upon treatment with thiophenol or neomenthyl mercaptane, chloroacetand propionamides with an additional Nor S-donor substituent in the amine part gave new multidentate ligands readily undergoing direct cyclopalladation in the reaction with PdCl2(NCPh)2. The realization of κ3-X, N, S-coordination (X = N, S) in the complexes obtained was confirmed by IR and NMR spectroscopy and, in some cases, by single-crystal X-ray crystallography. The evaluation of catalytic activity of the palladocycles in the Suzuki cross-coupling of aryl bromides with PhB(OH)2 allowed us to establish the principal structure—activity correlations.

Synthesis of Chiral Hydroxythiols Based on Oxygen-Containing α- and β-Pinene Derivatives

Isomeric 10-thiopinan-3-ols including (1S,2S,3S,5R)-6,6-dimethyl-2-(sulfanylmethyl)bicyclo[3.1.1]heptan-3-ol were synthesized for the first time from oxygen-containing α- and β-pinene derivatives.

Reaction of monoterpene hydroxy thiols with chlorine dioxide

Reactions of isobornane and pinane hydroxy thiols with chlorine dioxide have been studied. Unlike pinane derivatives, hydroxy thiols of the isobornane series reacted with chlorine dioxide to give the corresponding sulfinyl derivatives with high stereoselectivity. New terpenoids containing sulfur, oxygen, and chlorine atoms have been synthesized by oxidation of hydroxy thiols with chlorine dioxide.

Synthesis of neomenthylsulfanylimidazoles

2-Neomenthylsulfanyl-1H-imidazole,1-methyl-2-neomenthylsulfanyl-1H-imidazole, and 2-neomenthylsulfanyl-1H-benzimidazole were synthesized.

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.

Synthesis of 4,5-Epoxycaryophyll-9-Yl-Methanethiol and Sulfides Based on It

Epoxycaryophyll-9-yl-methaneethanethioate and epoxycaryophyll-9-yl-methanethiol were synthesized selectively in yields of 89 and 95%, respectively. Sulfides with aliphatic and aromatic fragments were synthesized in yields up to 89% via S-alkylation of 4,5-epoxycaryophyll-9-yl-methanethiol.

Caryophyllane thiols, vinyl thioethers, di- and bis-sulfides: antioxidant and membrane protective activities

Caryophyllane thioterpenoids were synthesized in 23 – 81% yields. The antioxidant properties of the obtained compounds in various model systems were found. It was revealed that 4,5‐epoxycaryophyll‐9‐ylmethanethiol has the greatest antioxidant activity. The isomerism of sesquiterpenic fragments was shown to have a significant effect on the biological activity of the compounds.

STEREOSELECTIVE SYNTHESIS OF CARANE-TYPE HYDROXYTHIOLS AND DISULFIDES BASED ON THEM

Isomeric 10-sulfanylcaran-4-ols and 4-sulfanylcaran-3-ols were synthesized and used to prepare disulfides in high yields.