Synthesis Of Carbocyclic Nucleoside Analogues Research Articles

From Heterocycles to Carbacycles: Synthesis of Carbocyclic Nucleoside Analogues from Enals and Hydroxylamines.

Substituted and stereochemically dense carbacycles can be prepared by sequential dipolar cycloaddition and reductive cleavage from enals and hydroxylamines. The reaction sequence proceeds with high efficiency for a wide variety of enals and hydroxylamines. The reaction is regio- and diastereoselective for the initial formation of a bridged bisisoxazolidine intermediate, which then undergoes quantitative double N-O cleavage to produce carbacycles as single diastereomers.

ChemInform Abstract: Synthesis of Carbocyclic Nucleoside Analogues with Five‐Membered Heterocyclic Nucleobases.

AbstractPyrazole amide (IV) shows modest anti‐HIV‐1 activity (EC50=24 μM).

Synthesis of carbocyclic nucleoside analogs with five-membered heterocyclic nucleobases

New carbocyclic nucleoside analogs with five-membered heterocyclic nucleobases were synthesized and evaluated as potential anti-HIV and anti-HCV agents. Among the synthesized carbocyclic nucleoside analogs, the pyrazole amide 15f exhibited modest selective anti-HIV-1 activity (EC50=24μM).

#Nitrosocarbonyls 1: antiviral activity of N-(4-hydroxycyclohex-2-en-1-yl)quinoline-2-carboxamide against the influenza A virus H1N1.

Influenza virus flu A H1N1 still remains a target for its inhibition with small molecules. Fleeting nitrosocarbonyl intermediates are at work in a short-cut synthesis of carbocyclic nucleoside analogues. The strategy of the synthetic approaches is presented along with the in vitro antiviral tests. The nucleoside derivatives were tested for their inhibitory activity against a variety of viruses. Promising antiviral activities were found for specific compounds in the case of flu A H1N1.

ChemInform Abstract: Synthesis of Carbocyclic Nucleoside Analogues by Palladium-Mediated Coupling.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Chiral Synthesis of Carbocyclic Nucleoside Analogs from Noncarbohydrate Precursors

Nucleosides represent a very important group of molecules, both chemically and biologically. Over the past forty years, the continued success of nucleoside analogs as chemotherapeutic agents has been both the result of and the driving force for the development of new synthetic methodologies to access analogs that may differ considerably from natural nucleosides. Among the many classes of nucleoside analogs that have been prepared and evaluated, carbocyclic nucleosides featured diverse and challenging syntheses and interesting biological activity. Carbohydrate chemistry has been elegantly and thoroughly exploited for the synthesis of carbocyclic nucleoside analogs, thanks to the availability and versatility of highly functionalized chiral precursors. In a number of examples, however, the synthesis of carbocyclic nucleosides has been elegantly and efficiently achieved from non-carbohydrate starting materials, either from natural optically active molecules, via chemical or enzymatic desymmetrization of prochiral molecules, or resolution of racemates. This review will discuss chiral syntheses of carbocyclic nucleoside analogs from non-carbohydrate precursors. Keywords: cyclopentyl nucleosides, ring-closing metathesis, ribavirin, enzymatic acetylation, Candida sp.

New Convergent Synthesis of Carbocyclic Nucleoside Analogues

AbstractFor Abstract see ChemInform Abstract in Full Text.

New Convergent Synthesis of Carbocyclic Nucleoside Analogues

Two convergent approaches towards the synthesis of carbocyclic nucleoside analogs will be described. Both approaches start from the stereochemically pure cyclopentenol 8 that has been prepared enantioselectively from an alkylated cyclopentadiene. Using these approaches, carbocyclic analogues of dT, FdU and BVdU have been prepared. Moreover, the conversion into the cycloSal-pronucleotide and the corresponding nucleotide will be presented for one example.

ChemInform Abstract: Highly Efficient and Enantioselective Synthesis of Carbocyclic Nucleoside Analogues Using Selective Early Transition Metal Catalysis.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Highly Efficient and Enantioselective Synthesis of Carbocyclic Nucleoside Analogs Using Selective Early Transition Metal Catalysis

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTHighly Efficient and Enantioselective Synthesis of Carbocyclic Nucleoside Analogs Using Selective Early Transition Metal CatalysisLuis E. Martínez, William A. Nugent, and Eric N. JacobsenView Author Information Harvard University, Department of Chemistry and Chemical Biology, Cambridge, Massachusetts 02138, and DuPont Central Research & Development, Wilmington, Delaware 19880 Cite this: J. Org. Chem. 1996, 61, 22, 7963–7966Publication Date (Web):November 1, 1996Publication History Received2 July 1996Published online1 November 1996Published inissue 1 January 1996https://doi.org/10.1021/jo961241lCopyright © 1996 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1096Altmetric-Citations35LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (193 KB) Get e-AlertsSUBJECTS:Catalysts,Ethers,Metathesis,Nucleic acids,Organic reactions Get e-Alerts

Synthesis of (1R, cis)-3-aminomethyl-1,2,2-trimethylcyclopentane-methanol: Two approaches using α-camphidone

(1R)-α-camphidone has proved to be extremely resistant to alkaline and acid hydrolysis, but the latter can be accomplished under drastic conditions. The aminoacid so obtained was transformed into the aminoalcohol 3, a desirable intermediate in the synthesis of carbocyclic nucleoside analogues. Alternatively, the N-tosyl derivative of α-camphidone can be reductively cleaved under mild conditions and the resulting tosylaminoalcohol converted into 3 in good yield.

Synthesis of Carbocyclic Nucleoside Analogues by Palladium-Mediated Coupling.

Synthesis of Carbocyclic Nucleoside Analogues by Palladium-Mediated Coupling.