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Synthesis 2018; 50(06): 1264-1274
DOI: 10.1055/s-0036-1591732
DOI: 10.1055/s-0036-1591732
paper
Stereoselective Synthesis of 1′,2′-cis-Disubstituted Carbocyclic ribo-Nucleoside Analogues
The authors are grateful to Universität Hamburg and the Italian MIUR fund – (PRIN 2009, Prot. N. 20094Bj9R7_002) for financial support.Further Information
Publication History
Received: 15 October 2017
Accepted after revision: 03 November 2017
Publication Date:
20 December 2017 (online)
Abstract
Herein we disclose an efficient strategy for the convergent synthesis of 1′,2′-cis-disubstituted carbocyclic ribo-nucleoside analogues. Starting from an enantiomerically pure cyclopentenol precursor, the key step for the preparation of the highly functionalized carbocyclic building block is an asymmetric dihydroxylation. Employing different variants of the Mitsunobu protocol, the condensation with all-natural nucleobases or their precursors affords a series of ribo-configured carbocyclic 1′,2′-cis-disubstituted nucleoside analogues.
Key words
stereoselective synthesis - carbocyclic nucleosides - asymmetric dihydroxylation - Mitsunobu reaction - heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591732.
- Supporting Information
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