Enantiodivergent synthesis of cyclohexenyl nucleosides

Èric Ferrer; Ramon Alibés; Félix Busqué; Marta Figueredo; Josep Font; Pedro De March

doi:10.1021/jo802492g

Enantiodivergent synthesis of cyclohexenyl nucleosides

Èric Ferrer, Ramon Alibés, Félix Busqué, Marta Figueredo, Josep Font, Pedro De March

Department of Chemistry

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

16 Citations (Scopus)

Abstract

An enantiodivergent synthesis of several cyclohexenyl nucleosides has been efficiently completed starting from the enantiopure hydrobenzoin-derived monoketal of cyclohex-2-en-1,4-dione, (+)-5. Stereodiversity was accomplished on the base coupling step. This methodology has proved to be useful for the synthesis of enantiopure pyrimidine and purine nucleoside analogues, which anti-HIV activity has been evaluated. © 2009 American Chemical Society.

Original language	English
Pages (from-to)	2425-2432
Journal	Journal of Organic Chemistry
Volume	74
Issue number	6
DOIs	https://doi.org/10.1021/jo802492g
Publication status	Published - 20 Mar 2009

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10.1021/jo802492g

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abstract = "An enantiodivergent synthesis of several cyclohexenyl nucleosides has been efficiently completed starting from the enantiopure hydrobenzoin-derived monoketal of cyclohex-2-en-1,4-dione, (+)-5. Stereodiversity was accomplished on the base coupling step. This methodology has proved to be useful for the synthesis of enantiopure pyrimidine and purine nucleoside analogues, which anti-HIV activity has been evaluated. {\textcopyright} 2009 American Chemical Society.",

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AU - Ferrer, Èric

AU - Alibés, Ramon

AU - Busqué, Félix

AU - Figueredo, Marta

AU - Font, Josep

AU - De March, Pedro

PY - 2009/3/20

Y1 - 2009/3/20

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AB - An enantiodivergent synthesis of several cyclohexenyl nucleosides has been efficiently completed starting from the enantiopure hydrobenzoin-derived monoketal of cyclohex-2-en-1,4-dione, (+)-5. Stereodiversity was accomplished on the base coupling step. This methodology has proved to be useful for the synthesis of enantiopure pyrimidine and purine nucleoside analogues, which anti-HIV activity has been evaluated. © 2009 American Chemical Society.

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DO - 10.1021/jo802492g

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Enantiodivergent synthesis of cyclohexenyl nucleosides

Abstract

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