Enantioselective synthesis of homocarbocyclic-2′-oxo-3′-azanucleosides

Chiacchio, Ugo; Saita, Maria Grazia; Crispino, Lia; Gumina, Giuseppe; Mangiafico, Sebastiano; Pistarà, Venerando; Romeo, Giovanni; Piperno, Anna; Clercq, Erik De

doi:10.1016/j.tet.2005.10.075

Cited by 29 publications

(11 citation statements)

References 21 publications

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“…For the use of nitrones in the spin-trapping technique and in organic synthesis, see: Janzen (1971); Zubarev (1979); Balasubramanian (1985); Pisaneschi et al (2002); Jones et al (2000); Bernotas et al (1999); Ali & Wazeer (1988); Merino (2005); Chiacchio et al (2006); Revuelta et al (2008); Astolfi et al (2003); Greci et al (2001); Tommasi et al (1999); Bruni et al (1998). For a related structure, see: Yamada et al (2003).…”

Section: Related Literaturementioning

confidence: 99%

“…On this basis, enantioselective syntheses of homo-carboxylic-2'-oxo-3'-azo-nucleosides were achieved by cycloaddition reactions of N-glycosyl nitrones with allylic nucleobases (Chiacchio et al, 2006). Moreover, a series of 3-spirocyclopropane dihydro-and tetrahydropyrid-4-ones were synthesized by nitrone cycloaddition to 1,1'-bicyclopropylidene (Revuelta et al, 2008).…”

Section: Commentmentioning

confidence: 99%

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3-Benzyl-3-hydroxy-2-phenyl-3H-indole 1-oxide

et al. 2010

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The asymmetric unit of the title compound, C21H17NO2, contains two crystallographically independent molecules of similar geometry. The indole ring systems form dihedral angles of 8.30 (5) and 9.58 (5)° with the attached phenyl rings, and 56.96 (5) and 57.68 (5)° with the aromatic rings of the respective benzyl groups. The molecular conformations are stabilized by intramolecular C—H⋯O hydrogen bonds. In the crystal structure, centrosymmetrically related pairs of molecules are linked into dimers through pairs of intermolecular O—H⋯O hydrogen bonds, generating 12-membered rings with R 2 2(12) motifs. The dimers are further linked into a three-dimensional network by C—H⋯O interactions.

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Section: Related Literaturementioning

confidence: 99%

Section: Commentmentioning

confidence: 99%

3-Benzyl-3-hydroxy-2-phenyl-3H-indole 1-oxide

et al. 2010

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“…The enantioselective synthesis of homonucleosides has been recently accomplished starting from N-ribosyl nitrone 106 (Schemes 19, 23) [39]. Cycloaddition of 106 with 1allylthymine or 1-allyl-5-fluorouracil gave all the four possi- and α-isomer ble isomers 124, 125, 126, 127 in 11:11:75:3 ratio (for the thymine derivative).…”

Section: Isoxazolidinyl Nucleosidesmentioning

confidence: 99%

Chiral Synthesis of Heterosubstituted Nucleoside Analogs from Noncarbohydrate Precursors

Casu¹,

Chiacchio²,

Romeo³

et al. 2007

COC

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The discovery of the potent antiviral activity of oxathiolanyl and dioxolanyl nucleosides prompted the extensive exploration of the chemistry and biology of heterosubstituted nucleoside analogs, in which the sugar moiety is replaced by a diheterocyclic ring. Carbohydrate-based synthetic approaches allowed the stereoselective synthesis of enantiomerically pure Dand L-analogs. However, due to the chemical nature of these molecules, approaches based on non-chiral starting materials and including chemical or enzymatic resolution steps proved advantageous for large scale syntheses. For the synthesis of isoxazolidinyl nucleosides, 1,3-dipolar cycloaddition has been a favorite approach, and the necessity to obtain optically active molecules has been addressed by asymmetric induction using chiral dipoles or dipolarophiles. This review will summarize the most interesting syntheses of heterosubstituted nucleoside analogs from non-carbohydrate precursors.

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“…Furthermore, the anthracene moiety could eventually intercalate the ds since it is well known its behaviour as an intercalating agent. 1,2,19 In order to dive into the mechanism of action of 8b, we are pursuing binding assays on isolated E2 protein and dsDNA chains on both the synthesized regioisomeric compounds as well as on the starting aminols and anthracene derivatives for the sake of comparison.…”

Section: Introductionmentioning

confidence: 99%