ChemInform Abstract: Enantiomerically Pure Chiral Building Blocks for Syntheses of Carbocyclic Nucleoside Analogues: A Formal Synthesis of Aristeromycin.

ChemInform ◽  
2010 ◽  
Vol 25 (14) ◽  
pp. no-no
Author(s):  
G. HELMCHEN ◽  
A. KROTZ ◽  
H.-P. NEUMANN ◽  
M. L. ZIEGLER
Keyword(s):  
Building Blocks ◽  
Nucleoside Analogues ◽  
Formal Synthesis ◽  
Enantiomerically Pure ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues

Synthesis of Enantiomerically Pure 1′,2′-cis-dideoxy, -dideoxydi­dehydro, -ribo and -deoxy Carbocyclic Nucleoside Analogues

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2266-2280 ◽  
Author(s):  
Chris Meier ◽  
Simon Weising ◽  
Patrick Dekiert ◽  
Dominique Schols ◽  
Johan Neyts
Keyword(s):  
Stereospecific Synthesis ◽  
Nucleoside Analogues ◽  
Enantiomerically Pure ◽  
Type Reaction ◽  
Microwave Assisted ◽  
Synthetic Strategy ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues

We describe a short and stereospecific synthesis of different series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues. All-natural nucleobases or their precursors are coupled in a microwave-assisted Mitsunobu-type reaction with enantiomerically pure (1R,2S)-2-(benzyloxymethyl)cyclopent-3-enol. By modifying the cyclopentene scaffold, our synthetic strategy gives access to a series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues of the dideoxy (dd), di­deoxydidehydro (d4) or the ribo series. The ribo series is synthesized in a more convenient way compared to a previous route. The deoxy series of 1′,2′-cis-disubstituted carbocyclic nucleoside analogues is prepared following an earlier reported approach. This synthesis involves the microwave-assisted coupling of (1R,2S,3S)-3-(benzyloxy)-2-[(benzyl­oxy)methyl]cyclopentan-1-ol with the appropriate nucleobases.

Synthesis of novel racemic carbocyclic nucleoside analogues derived from 4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol and 4-oxatricyclo[4.3.1.03,7]decane-10-methanol, compounds with activity against Coxsackie viruses

2009 ◽  
Vol 74 (3) ◽  
pp. 469-485 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Martin Dračínský ◽  
Armando M. De Palma ◽  
Johan Neyts ◽  
Antonín Holý
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Purine Nucleoside ◽  
Nucleoside Analogues ◽  
Lithium Aluminium Hydride ◽  
Subsequent Reduction ◽  
Lithium Aluminium ◽  
Diels Alder Reaction ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues

(1R*,2R*,3R*,4S*)-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dimethanol (10) and (1R*,2R*,3R*,4S*)-bicyclo[2.2.2]oct-5-ene-2,3-dimethanol (14), which were prepared by the Diels–Alder reaction and subsequent reduction with lithium aluminium hydride, were treated with benzyl azidoformate to give benzylN-[(1R*,2R*,3S*,6S*,7S*,9S*)-9-(hydroxymethyl)-4,8-dioxatricyclo[4.2.1.03,7]nonan-2-yl]carbamate (11) and benzylN-[(1R*,2R*,3R*,6R*,7S*,10S*)-10-(hydroxymethyl)-4-oxatricyclo[4.3.1.03,7]decan-2-yl]carbamate (15). Hydrogenolysis of carbamates11or15afforded (1R*,2R*,3S*,6S*,7S*,9S*)-2-amino-4,8-dioxatricyclo[4.2.1.03,7]nonane-9-methanol (12) or (1R*,2R*,3R*,6R*,7S*,10S*)-2-amino-4-oxatricyclo[4.3.1.03,7]decane-10-methanol (16). The amines12and16were transformed to thymine and purine nucleoside analogues. The target compounds were tested for the activity againstCoxsackievirus.

ChemInform Abstract: Unsaturated and Carbocyclic Nucleoside Analogues: Synthesis, Antitumor, and Antiviral Activity.

ChemInform ◽  
2010 ◽  
Vol 22 (24) ◽  
pp. no-no
Author(s):  
S. PHADTARE ◽  
D. KESSEL ◽  
T. H. CORBETT ◽  
H. E. RENIS ◽  
B. A. COURT ◽  
...  
Keyword(s):  
Antiviral Activity ◽  
Nucleoside Analogues ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues

ChemInform Abstract: Asymmetric Synthesis of Novel Apio Carbocyclic Nucleoside Analogues as Potential Antiviral and Antitumor Agent

ChemInform ◽  
2008 ◽  
Vol 39 (11) ◽  
Author(s):  
Lak Shin Jeong ◽  
Jeong A. Lee ◽  
Hyung Ryong Moon ◽  
Hea Ok Kim ◽  
Kang Man Lee ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Antitumor Agent ◽  
Nucleoside Analogues ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues

A Novel Approach to Khantiokerically Pure Carbocyclic Nucleoside Analogues

1987 ◽  
Vol 6 (1-2) ◽  
pp. 233-237 ◽  
Author(s):  
Michael Bodenteich ◽  
Kurt Faber ◽  
Gerhard Penn And ◽  
Herfried Griengl
Keyword(s):  
Nucleoside Analogues ◽  
Novel Approach ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues

Asymmetric Synthesis of Novel Apio Carbocyclic Nucleoside Analogues as Potential Antiviral and Antitumor Agent

2007 ◽  
Vol 26 (6-7) ◽  
pp. 721-724 ◽  
Author(s):  
Lak Shin Jeong ◽  
Jeong A. Lee ◽  
Hyung Ryong Moon ◽  
Hea Ok Kim ◽  
Kang Man Lee ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Antitumor Agent ◽  
Nucleoside Analogues ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues

ChemInform Abstract: An Efficient Organometallic Approach to New Carbocyclic Nucleoside Analogues.

ChemInform ◽  
2010 ◽  
Vol 33 (26) ◽  
pp. no-no
Author(s):  
Juraj Velcicky ◽  
Johann Lex ◽  
Hans-Guenther Schmalz
Keyword(s):  
Nucleoside Analogues ◽  
Carbocyclic Nucleoside ◽  
Carbocyclic Nucleoside Analogues
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