Highly stereoselective synthesis of novel cyclobutane-fused azanucleosides

Ramon Flores; Ramon Alibés; Marta Figueredo; Josep Font

doi:10.1016/j.tet.2009.06.067

Highly stereoselective synthesis of novel cyclobutane-fused azanucleosides

Ramon Flores, Ramon Alibés, Marta Figueredo, Josep Font

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

13 Citations (Scopus)

Abstract

Stereoselective syntheses of several 3-azabicyclo[3.2.0]heptane nucleoside analogues have been efficiently completed starting from a homochiral a,b-unsaturated-g-lactam. The target compounds were prepared by condensation of a common bicyclic acetate intermediate with pyrimidine and purine bases under modified Vorbrüggen conditions. The anti-HIV activity of the newly synthesized azanucleosides has been evaluated. © 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6912-6917
Journal	Tetrahedron
Volume	65
Issue number	34
DOIs	https://doi.org/10.1016/j.tet.2009.06.067
Publication status	Published - 22 Aug 2009

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10.1016/j.tet.2009.06.067

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abstract = "Stereoselective syntheses of several 3-azabicyclo[3.2.0]heptane nucleoside analogues have been efficiently completed starting from a homochiral a,b-unsaturated-g-lactam. The target compounds were prepared by condensation of a common bicyclic acetate intermediate with pyrimidine and purine bases under modified Vorbr{\"u}ggen conditions. The anti-HIV activity of the newly synthesized azanucleosides has been evaluated. {\textcopyright} 2009 Elsevier Ltd. All rights reserved.",

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AU - Flores, Ramon

AU - Alibés, Ramon

AU - Figueredo, Marta

AU - Font, Josep

PY - 2009/8/22

Y1 - 2009/8/22

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AB - Stereoselective syntheses of several 3-azabicyclo[3.2.0]heptane nucleoside analogues have been efficiently completed starting from a homochiral a,b-unsaturated-g-lactam. The target compounds were prepared by condensation of a common bicyclic acetate intermediate with pyrimidine and purine bases under modified Vorbrüggen conditions. The anti-HIV activity of the newly synthesized azanucleosides has been evaluated. © 2009 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tet.2009.06.067

DO - 10.1016/j.tet.2009.06.067

M3 - Article

SN - 0040-4020

VL - 65

SP - 6912

EP - 6917

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Highly stereoselective synthesis of novel cyclobutane-fused azanucleosides

Abstract

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