AI Article Synopsis
- Carbocyclic nucleosides are modified nucleosides featuring a carbocycle instead of a furanoside, with several examples found in nature, particularly those with 5-membered rings.
- The review analyzes various techniques for creating 3- to 6-membered carbocycles, emphasizing the synthesis and functionalization of 5-membered rings and how they relate to nucleoside development.
- Synthesis methods for 5-membered rings are categorized into two types: those formed by ring-closing reactions and those using pre-existing rings, while relevant enantioselective techniques for 3-, 4-, and 6-membered rings are also discussed.
Article 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Carbocyclic nucleosides are nucleoside analogues in which the furanosidic moiety has been replaced by a carbocycle.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=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.
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| http://dx.doi.org/10.1039/c3cs00003f | DOI Listing |
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