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Synthesis 2018; 50(11): 2266-2280
DOI: 10.1055/s-0037-1609493
DOI: 10.1055/s-0037-1609493
paper
Synthesis of Enantiomerically Pure 1′,2′-cis-dideoxy, -dideoxydidehydro, -ribo and -deoxy Carbocyclic Nucleoside Analogues
The authors are grateful to Universität Hamburg for financial support.Further Information
Publication History
Received: 25 January 2018
Accepted after revision: 06 March 2018
Publication Date:
12 April 2018 (online)
Abstract
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.
Key words
carbocycles - Mitsunobu coupling - 1′,2′-cis-substitution - microwave reaction - nucleosidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609493.
- Supporting Information
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