The Unabated Synthesis of New Nucleoside Analogues with Antiviral Potential: A Tribute to Morris J. Robins

Clercq, Erik De

doi:10.1080/15257770903054159

Cited by 21 publications

(1 citation statement)

References 45 publications

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“…There has been long-standing interest in the synthesis of non-natural analogs of nucleosides. The modified nucleosides, or their nucleotide or oligonucleotide analogs, have been widely explored as pharmaceutically active compounds [1,2,3,4], in the study of carcinogenesis mechanisms [5,6,7], and to incorporate probe functionality in DNA and RNA [8,9,10,11]. Nucleoside derivatives can be made through manipulation of the sugar moiety, replacement of the purine or pyrimidine heterocycle, or through covalent modification of the natural heterocyclic base or their analogs.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides

Shaughnessy

2015

Molecules

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Synthetic modification of nucleoside structures provides access to molecules of interest as pharmaceuticals, biochemical probes, and models to study diseases. Covalent modification of the purine and pyrimidine bases is an important strategy for the synthesis of these adducts. Palladium-catalyzed cross-coupling is a powerful method to attach groups to the base heterocycles through the formation of new carbon-carbon and carbon-heteroatom bonds. In this review, approaches to palladium-catalyzed modification of unprotected nucleosides, nucleotides, and oligonucleotides are reviewed. Polar reaction media, such as water or polar aprotic solvents, allow reactions to be performed directly on the hydrophilic nucleosides and nucleotides without the need to use protecting groups. Homogeneous aqueous-phase coupling reactions catalyzed by palladium complexes of water-soluble ligands provide a general approach to the synthesis of modified nucleosides, nucleotides, and oligonucleotides.

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Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides

Shaughnessy

2015

Molecules

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Recent Advances in Transition‐Metal‐Catalyzed Functionalization of 1‐Thiosugars

2018

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Thioglycosides are valuable glycomimetic derivatives that have attracted much attention as mimetics of O-glycosides. Thioglycosides are among the most important glycomimetics reported to date due to their powerful activities. Owing to their importance, building up methods for their construction has drawn considerable attention. However, the classical methods of their synthesis presenting many shortcomings such as the use of harsh acidic media, and are generally limited in substrate scope. Therefore, metal-catalyzed coupling of thiosugars with halogenated electrophiles can be a superior and highly versatile approach to the sunthesis of thioglycosides. The central objective of this Focus Review is to highlight metal-catalyzed reactions for the creation of aromatic and heteroaromatic thioglycosides.

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Carbazole‐Based N‐Heterocyclic Carbenes for the Promotion of Copper‐Catalyzed Palladium‐Free Homo‐/Hetero‐Coupling of Alkynes and Sonogashira Reactions

et al. 2020

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Alkynes are useful synthetic building blocks that occur in many naturally occurring molecules and have the potential to be easily modified for further natural products and drug synthesis applications. Given the‐versatility of the alkyne functionality,‐various synthetic methods (mostly palladium‐based) are known in the literature, allowing the installation to take place under different reaction conditions. A single catalytic system (without Pd) however, if developed could provide a single point solution for the installation of the alkyne moiety and keeping this in mind, we report herein a highly active palladium‐free Cu/carbazole‐based NHC catalyst system allowing homocoupling and heterocoupling of alkynes at ambient temperature. Using a combination of Cu/NHC‐catalyzed homocoupling/deprotection/heterocoupling sequence tetraynes have also been synthesized in good yields. The Cu/NHC catalyst system was also able to catalyze a palladium‐free Sonogashira reaction of synthetically useful nucleosides.

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The Unabated Synthesis of New Nucleoside Analogues with Antiviral Potential: A Tribute to Morris J. Robins

Abstract: The furo[2,3-d]pyrimidin-2(3H)-one is the key structural determinant in the exquisitely potent activity of its derivatives (R = 2-deoxyribosyl; R' = p-pentylphenyl) against VZV (varicella-zoster virus) replication. [structure: see text].

Cited by 21 publications

References 45 publications

Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides

Palladium-Catalyzed Modification of Unprotected Nucleosides, Nucleotides, and Oligonucleotides

Recent Advances in Transition‐Metal‐Catalyzed Functionalization of 1‐Thiosugars

Carbazole‐Based N‐Heterocyclic Carbenes for the Promotion of Copper‐Catalyzed Palladium‐Free Homo‐/Hetero‐Coupling of Alkynes and Sonogashira Reactions

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