Stereoselective synthesis of chiral precursors to cyclobutane carbocyclic nucleosides and oligopeptides

Rouge, Pablo D.; Moglioni, Albertina G.; Moltrasio, Graciela Y.; Ortuño, Rosa M.

doi:10.1016/s0957-4166(02)00823-6

Cited by 22 publications

(9 citation statements)

References 29 publications

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“…Cyclobutanols were obtained by controlled hydrolysis of the corresponding acetates using cold potassium hydroxide in methanol. The compounds 1a and 4a were already described by us [24] and the spectroscopical data of compounds 1b and 4b were in accordance with those reported previously for their enantiomers. [25] Despite the unselective nature of RuO 4 as an oxidant, there are reports of the oxidation of cyclobutanic compounds using ruthenium-based oxidants.…”

Section: Resultssupporting

confidence: 89%

Differential Oxidation Conditions of Substituted Cyclobutanols Derived from Terpenes

Kuran

Moglioni

2014

Synthetic Communications

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Section: Resultssupporting

confidence: 89%

Differential Oxidation Conditions of Substituted Cyclobutanols Derived from Terpenes

Kuran

Moglioni

2014

Synthetic Communications

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“…336 On the other hand, Schmidt rearrangement 338 of ketoester derivative 917 obtained from commercially available (S)-verbenone 59 using NaN 3 /MeSO 3 H produced acetylated amine derivative 918 in 75% yield, which by acidic hydrolysis led to (1S,3R)-3-amino-2,2-dimethylcyclobutanecarboxylic acid 919 in 83% yield (Scheme 229). 339 More recently, Ló pez et al 340 have described the stereoselective synthesis of (1R,3S)-919 from commercially available a-pinene. In this context, oxidation of a-pinene produced keto-acid derivative 920, 59 which by treatment with hydroxylamine-O-sulfonic acid followed by a Beckmann rearrangement and subsequent esterification gave N-acetyl amino derivative 921.…”

Section: Synthesis Of C N A;c Derivativesmentioning

confidence: 99%

Stereoselective synthesis of γ-amino acids

Ordóñez

Cativiela

2007

Tetrahedron: Asymmetry

248

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“…Another example of a synthetic pathway used to synthesize chiral precursors of cyclobutane nucleosides was recently reported by Ortuno et al [39] when, starting from the (À)-(S)-vebenone, the hydroxy-and amino-cyclobutane derivatives were obtained.…”

Section: G)mentioning

confidence: 99%

Synthesis and Biological Activity of Selected Carbocyclic Nucleosides

Mieczkowski

Agrofoglio

2008

Modified Nucleosides

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Nucleoside analogues are extremely useful for the development of therapeutic agents to control viral diseases and cancer. Replacement the oxygen of furanose ring of a nucleoside by a CH 2 unit results in carbocyclic nucleoside analogues. Carbocyclic nucleosides have emerged as targets of intense investigation due to their potent biological activity and greater metabolic activity and stability to nucleoside phosphorylases than the corresponding carbohydrate counterpart. Among these, aristeromycin (1), neplanocin (2), abacavir (3), lobucavir (4), synguanol (5) or the newly FDA-approved anti-HBV Baraclude Ò (6, Entecavir) ( Figure 15.1) are a few of the carbocyclic nucleosides that are useful antiviral drugs.The cellular processing and mechanism of action of carbocyclic nucleosides are, in general, similar to those of conventional nucleosides. They may undergo progressive phosphorylation to the corresponding mono-, di-, and triphosphates, and any of these activated forms may interact with natural cellular processes (Figure 15.2). On occasion, the interaction is innocuous and has little or no effect upon cell viability, but very often a significant inhibition of essential biochemical reactions occurs and in these cases measurable effects will be observable.One class of cellular enzymes to which carbocyclic nucleosides are not susceptible is the nucleoside phosphorylases, as a consequence of which they are extremely stable towards sugar-base cleavage. Most of those carbocyclic nucleosides which have been studied intensively are active as inhibitors of a viral enzyme (mainly a polymerase). Experience has shown that the essential structural features of carbocyclic nucleosides which must be retained are: the ability of the base to engage in base pairing with its DNA partner, and the presence of a 5 0 -hydroxyl group (or equivalent) which is capable of phosphorylation. The remainder of the sugar component can be regarded as a scaffold which ensures that the base pairing functionality and the 5 0 -phosphate (or phosphonate) are well distributed in space. The carbocyclic nucleosides do not have the same conformational data as the parent nucleosides; rather, in all cases they Modified Nucleosides: in Biochemistry, Biotechnology and Medicine. Edited by Piet Herdewijn

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Stereoselective synthesis of chiral precursors to cyclobutane carbocyclic nucleosides and oligopeptides

Cited by 22 publications

References 29 publications

Differential Oxidation Conditions of Substituted Cyclobutanols Derived from Terpenes

Differential Oxidation Conditions of Substituted Cyclobutanols Derived from Terpenes

Stereoselective synthesis of γ-amino acids

Synthesis and Biological Activity of Selected Carbocyclic Nucleosides

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