Efficient Synthesis of New Nucleoside Analogues with a Methylenecyclobutane Unit

Danappe, Sophie; Boeda, Fabien; Alexandre, Christian; Aubertin, Anne-Marie; Bourgougnon, Nathalie; Huet, François

doi:10.1080/00397910600908918

Cited by 8 publications

(3 citation statements)

References 16 publications

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“…Path A is by far the most frequently practiced one, − as it starts from commercially available cyclobutanone ( 1276 ). Path B, − however, can take advantage of the in situ formation of the cyclobutylphosphonium ylide from the phosphonium salt obtained with 1,3-dibromobutane and 2 equiv of a base.…”

Section: Alkylidenecyclobutanesmentioning

confidence: 99%

“…Path B, − however, can take advantage of the in situ formation of the cyclobutylphosphonium ylide from the phosphonium salt obtained with 1,3-dibromobutane and 2 equiv of a base. The Wittig olefination has been used for the synthesis of protected MCB amino acids 1278 and 1279 , and as a route to the synthesis of MCB nucleosides 1280 – 1283 (Figure ) …”

Section: Alkylidenecyclobutanesmentioning

confidence: 99%

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Progress in the Synthesis and Transformations of Alkylidenecyclopropanes and Alkylidenecyclobutanes

et al. 2014

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Section: Alkylidenecyclobutanesmentioning

confidence: 99%

Section: Alkylidenecyclobutanesmentioning

confidence: 99%

Progress in the Synthesis and Transformations of Alkylidenecyclopropanes and Alkylidenecyclobutanes

et al. 2014

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“…The direct MR coupling of the two canonical purine nucleobases, adenine and guanine, is not, in most cases, the most applied methodology for nucleoside analog synthesis. Although adenine has been used as a pronucleophile, 43,[59][60][61][62] the strategy to obtain an adenine nucleoside relies mainly on the coupling of a nucleobase precursor, followed by transformation of the purine to adenine moiety.…”

Section: Purine Couplingmentioning

confidence: 99%

Nucleobase coupling by Mitsunobu reaction towards nucleoside analogs

Sousa¹,

Rauter²

2020

Arkivoc

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The coupling of a nucleobase is a key step in the synthesis of most nucleoside analogs, e.g. carbocyclic nucleosides, isonucleosides and acyclic nucleosides. The synthetic strategies for nucleosides based on Nglycosylation are not applied when the nucleobase is not linked to the anomeric center. Thus, other methods have been employed, mainly those based on the alkylation of nucleobases. The Mitsunobu reaction, in which a hydroxy group is replaced by a nucleophile, has also been extensively applied, generating a diversity of molecules, including pharmaceuticals and their precursors. In this review the usefulness of this reaction for the coupling of nucleobases to non-anomeric positions of sugars, carbasugars and other homocyclic and linear structures is highlighted and discussed, covering purines and pyrimidines as pronucleophiles.

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