Journal ArticleDOI
Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides
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TLDR
Asymmetric synthesis of L-carbocyclic nucleosides, (+)-β-L-aristeromycin (11 ) and its thymine analog (12 ) was accomplished as discussed by the authors.About:
This article is published in Tetrahedron Letters.The article was published on 1997-06-16. It has received 29 citations till now. The article focuses on the topics: Enantioselective synthesis & Enone.read more
Citations
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New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides
Journal ArticleDOI
Synthesis and conformational and biological aspects of carbasugars.
TL;DR: In this article, the progress made in the chemistry, synthesis and biology of carbasugars until May 2004 is discussed, including the extensively studied carbapyranoses as well as the scarcely considered carbafuranoses.
Journal ArticleDOI
The latest progress in the synthesis of carbocyclic nucleosides.
TL;DR: This review presents the latest developments in the field of carba-nucleosides (1994–1998) and special attention is paid to the synthesis of key precursors to those carBA-n nucleosides that possess significant biological activities or have novel structures.
Journal ArticleDOI
Enzymatic Resolution of Aminocyclopentenols as Precursors to d- and l-Carbocyclic Nucleosides
TL;DR: Racemic cis-4-aminocyclopent-2-en-1-ols were synthesized in three steps utilizing hetero Diels−Alder chemistry, kinetically resolved by enzymatic acetylation or hydrolysis, respectively.
Journal ArticleDOI
A novel, one-pot ring expansion of cyclobutanones. Syntheses of carbovir and aristeromycin.
Brian Brown,Louis S. Hegedus +1 more
TL;DR: A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3, which was successfully advanced to (+)-carbovir and (+)-aristeromycin.
References
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Journal ArticleDOI
Synthesis of carbocyclic nucleosides
Luigi A. Agrofoglio,Edouard Suhas,A. Farese,Roger Condom,S. Richard Challand,Robert A. Earl,Roger Guedj +6 more
Journal ArticleDOI
Synthesis of chiral carbocyclic nucleosides
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Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides.
Robert Vince,Mei Hua +1 more
TL;DR: Carbovir emerged as a potent and selective anti-HIV agent and its hydrolytic stability and its ability to inhibit the infectivity and replication of HIV in T-cells at concentrations of approximately 200-400-fold below toxic concentrations make carbovir an excellent candidate for development as a potential antiretroviral agent.
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Activities of the four optical isomers of 2',3'-dideoxy-3'-thiacytidine (BCH-189) against human immunodeficiency virus type 1 in human lymphocytes.
Raymond F. Schinazi,Chung K. Chu,A Peck,A. Mcmillan,R. Mathis,Deborah L. Cannon,L S Jeong,J W Beach,W.‐B. Choi,S Yeola +9 more
TL;DR: Four different isomers of 2',3'-dideoxy-3'-thiacytidine were evaluated in primary human lymphocytes infected with human immunodeficiency virus type 1 and the beta-L-(-) isomer was the most potent enantiomer, with a median effective concentration of 1.8 nM.
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Deoxycytidine deaminase-resistant stereoisomer is the active form of (+/-)-2',3'-dideoxy-3'-thiacytidine in the inhibition of hepatitis B virus replication.
Chien-Neng Chang,Shin-Lian Doong,Jing Zhou,J. W. Beach,L.S. Jeong,Chung K. Chu,C.H. Tsai,Yung-Chi Cheng,D Liotta,R Schinazi +9 more
TL;DR: This is the first nucleoside analog with the unnatural sugar configuration demonstrated to have antiviral activity and was found to have potent activity against human hepatitis B virus as well as human immunodeficiency viruses in culture.
Related Papers (5)
Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides.
Robert Vince,Mei Hua +1 more