Oxidative cleavage of an alkene with catalytic ruthenium tetroxide

10.1039/sp186 ◽  
2002 ◽  
Author(s):  
Meriel Kimberley
Keyword(s):  
Oxidative Cleavage ◽  
Ruthenium Tetroxide

Preparation of New Oxidized 18-α-Oleanane Derivatives

2005 ◽  
Vol 70 (9) ◽  
pp. 1447-1464 ◽  
Author(s):  
Miroslav Kvasnica ◽  
Iva Tišlerová ◽  
Jan Šarek ◽  
Jan Sejbal ◽  
Ivana Císařová
Keyword(s):  
Double Bond ◽  
Nmr Spectra ◽  
Biological Activities ◽  
Oxidative Cleavage ◽  
Allylic Oxidation ◽  
Unsaturated Ketone ◽  
Ruthenium Tetroxide ◽  
Unsaturated Compounds ◽  
Starting Compound ◽  
C Nmr

19β,28-Epoxy-4,5-seco-3,5-cyclo-18α-olean-3(5)-ene (2) is an appropriate compound for oxidations, which lead to new oxidized compounds with potential biological activities. Several oxidations were used such as epoxidation, allylic oxidation, oxidative cleavage of double bond and other ones. From the starting compound epoxides 3a, 3b and unsaturated ketone 4 were prepared. This ketone was further oxidized to diketone 6 and anhydride 7. The double bonds of all unsaturated compounds were cleaved with ruthenium tetroxide to afford new A-seco oleananes. The structure and stereochemistry of the compounds were derived from IR, MS, 1H and 13C NMR spectra (1D and 2D COSY, TOCSY, NOESY, HSQC, HMBC).

ChemInform Abstract: OXIDATIVE CLEAVAGE OF PARTIALLY OR PERFLUORINATED OLEFINS BY RUTHENIUM TETROXIDE

1979 ◽  
Vol 10 (23) ◽  
Author(s):  
C. GUIZARD ◽  
H. CHERADAME ◽  
Y. BRUNEL ◽  
C. G. BEGUIN
Keyword(s):  
Oxidative Cleavage ◽  
Ruthenium Tetroxide

Oxidative cleavage of 3β-acetoxy-21-oxolup-18-en-28-oic acid by ruthenium tetroxide

2010 ◽  
Vol 46 (4) ◽  
pp. 545-548
Author(s):  
M. Kvasnica ◽  
P. Spacilova ◽  
M. Budesinsky ◽  
M. Hajduch ◽  
J. Sarek
Keyword(s):  
Oxidative Cleavage ◽  
Ruthenium Tetroxide

Oxidative cleavage of partially or perfluorinated olefins by ruthenium tetroxide

1979 ◽  
Vol 13 (2) ◽  
pp. 175-177 ◽  
Author(s):  
Christian Guizard ◽  
Herve Cheradame ◽  
Yvon Brunel ◽  
Claude G. Beguin
Keyword(s):  
Oxidative Cleavage ◽  
Ruthenium Tetroxide

Structural integrity after cold storage of human epidermal model in hypothermosol: A correlative ultrastructural and fluorescent assay

1994 ◽  
Vol 52 ◽  
pp. 270-271
Author(s):  
Henry H. Eichelberger ◽  
John G. Baust ◽  
Robert G. Van Buskirk
Keyword(s):  
Cold Storage ◽  
Structural Integrity ◽  
Culture Media ◽  
Cell Structure ◽  
Natural State ◽  
Sodium Cacodylate ◽  
Ruthenium Tetroxide ◽  
Cacodylate Buffer ◽  
Before And After

For research in cell differentiation and in vitro toxicology it is essential to provide a natural state of cell structure as a benchmark for interpreting results. Hypothermosol (Cryomedical Sciences, Rockville, MD) has proven useful in insuring the viability of synthetic human epidermis during cold-storage and in maintaining the epidermis’ ability to continue to differentiate following warming.Human epidermal equivalent, EpiDerm (MatTek Corporation, Ashland, MA) consisting of fully differentiated stratified human epidermal cells were grown on a microporous membrane. EpiDerm samples were fixed before and after cold-storage (4°C) for 5 days in Hypothermosol or skin culture media (MatTek Corporation) and allowed to recover for 7 days at 37°C. EpiDerm samples were fixed 1 hour in 2.5% glutaraldehyde in sodium cacodylate buffer (pH 7.2). A secondary fixation with 0.2% ruthenium tetroxide (Polysciences, Inc., Warrington, PA) in sodium cacodylate was carried out for 3 hours at 4°C. Other samples were similarly fixed, but with 1% Osmium tetroxide in place of ruthenium tetroxide. Samples were dehydrated through a graded acetone series, infiltrated with Spurrs resin (Polysciences Inc.) and polymerized at 70°C.

Synthesis of (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(Carboxymethyl)]oxime, New Hapten for Dihydrotestosterone (17β-hydroxy-5α-androstan-3-one)

1997 ◽  
Vol 62 (10) ◽  
pp. 1642-1649 ◽  
Author(s):  
Ivan Černý ◽  
Tereza Slavíková ◽  
Vladimír Pouzar
Keyword(s):  
Hydroxy Group ◽  
Carboxy Group ◽  
Title Compound ◽  
Oxidative Cleavage ◽  
Hydroxy Derivative ◽  
Borohydride Reduction ◽  
Protecting Group ◽  
Free Hydroxy Group

Addition of 4-methoxybenzyl alcohol to 3β-hydroxy-5α-androst-15-en-17-one gave the mixture of isomeric 15-(4-methoxyphenyl)methoxy derivatives from which, after acetylation and chromatography, the major 15β isomer was separated. Borohydride reduction gave 17β-hydroxy derivative which was protected as methoxymethyl ether. Oxidative cleavage of protecting group at position 15 and the subsequent Jones oxidation afforded corresponding 15-ketone. Its oximation with O-(carboxymethyl)hydroxylamine, deacetylation and methylation with diazomethane gave protected O-(carboxymethyl)oxime derivative with free hydroxy group at position 3. Its oxidation afforded dihydrotestosterone derivative and successive deprotection of position 17 and of carboxy group led to final (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(carboxymethyl)]oxime. The title compound was designed as dihydrotestosterone hapten for heterologous radioimmunoassays.

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