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Issue 12, 2013
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Advances in the enantioselective synthesis of carbocyclic nucleosides

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Abstract

Carbocyclic nucleosides are nucleoside analogues in which the furanosidic moiety has been replaced by a carbocycle. Several members of this family have been isolated from natural sources and include a 5-membered ring carbocycle. The aim of this review is to examine critically the different methodologies for the enantioselective construction of 3- to 6-membered rings, with a particular focus on 5-membered rings and their modifications. The procedures for bonding the heterocyclic moiety and the carbohydrate are treated separately. The methods for synthesising the carbocyclic moiety mainly focus on the construction of the cycle, although precise details about the functionalisation are provided in some cases. The selected methods aim to provide an overview of the synthesis of carbocycles related to the synthesis of carbocyclic nucleosides. The methods of synthesis of 5-membered rings are classified into two types: methods in which the cyclopentane ring is formed by ring closing reactions (C[double bond, length as m-dash]C and C–C formation) and methods that start from preformed 5-membered rings, based mainly on cycloaddition reactions. With respect to the methods of synthesis of 3-, 4- and 6-membered ring carbocyclic nucleosides, a selection of the more relevant enantioselective procedures is presented in a systematic manner.

Graphical abstract: Advances in the enantioselective synthesis of carbocyclic nucleosides

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Article information


Submitted
02 Jan 2013
First published
07 Mar 2013

Chem. Soc. Rev., 2013,42, 5056-5072
Article type
Tutorial Review

Advances in the enantioselective synthesis of carbocyclic nucleosides

O. Boutureira, M. I. Matheu, Y. Díaz and S. Castillón, Chem. Soc. Rev., 2013, 42, 5056
DOI: 10.1039/C3CS00003F

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