Enantioselective synthesis of N,O-psiconucleosides

Chiacchio, Ugo; Borrello, Luisa; Iannazzo, Daniela; Merino, Pedro; Piperno, Anna; Rescifina, Antonio; Richichi, Barbara; Romeo, Giovanni

doi:10.1016/s0957-4166(03)00525-1

Cited by 33 publications

(14 citation statements)

References 22 publications

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“…5. In addition it is worthy of note that all reported cycloaddition reactions (1,3-DC) with D-glyceraldehyde derived nitrones and closely related compounds led to anti compounds [37]. By contrast, all organometallic addition reactions (NA) to the same nitrones in the absence of any Lewis acid led to syn adducts [4].…”

Section: Synthesis Of Nucleoside Analoguesmentioning

confidence: 99%

New developments in nucleophilic additions to nitrones

Merino

2005

Comptes Rendus. Chimie

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Section: Synthesis Of Nucleoside Analoguesmentioning

confidence: 99%

New developments in nucleophilic additions to nitrones

Merino

2005

Comptes Rendus. Chimie

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“…[6][7][8][9][10][11] Our research group has reported a versatile route towards the synthesis of N,O-psiconucleosides both in racemic and in enantiopure form. 5,[12][13][14][15] More recently, the use of a chiral auxiliary has promoted the enantioselective synthesis of a series of psiconucleosides. 16 However, none of the reported compounds has shown a remarkable biological activity, probably due to the lack of efficient phosphorylation towards the triphosphate derivatives, the active form of nucleoside RT inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Truncated phosphonated C-1′-branched N,O-nucleosides: A new class of antiviral agents

Romeo

Carnovale

Giofrè

et al. 2012

Bioorganic & Medicinal Chemistry

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a b s t r a c tTruncated phosphonated C-1 0 -branched N,O-nucleosides have been synthesized in good yields by 1,3-dipolar cycloaddition methodology, starting from N-methyl-C-(diethoxyphosphoryl)nitrone 7. Preliminary biological assays show that b-anomers are able to inhibit HIV in vitro infection at concentrations in the micromolar range. Higher SI values with respect to AZT indicated that the compounds were endowed with low cytotoxicity.

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“…Enantiomerically pure isoxazolidinyl psiconucleosides were prepared using nitrone 114 as chiral non-racemic starting material (Scheme 21) [37]. Cycloaddition proceeded with good control of E/Z diastereoselectivity and moderate diastereofacial selectivity, giving a mixture of three of the four possible isomers: Z-115, E-115 and 116 in 50, 15 and 25 % isolated yield, respectively.…”

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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Enantioselective synthesis of N,O-psiconucleosides

Cited by 33 publications

References 22 publications

New developments in nucleophilic additions to nitrones

New developments in nucleophilic additions to nitrones

Truncated phosphonated C-1′-branched N,O-nucleosides: A new class of antiviral agents

Chiral Synthesis of Heterosubstituted Nucleoside Analogs from Noncarbohydrate Precursors

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