Synthesis of purine nucleosides built on a 3-oxabicyclo[3.2.0]heptane scaffold

Ramon Flores; Albert Rustullet; Ramon Alibés; Angel Álvarez-Larena; Pedro De March; Marta Figueredo; Josep Font

doi:10.1021/jo200775x

Synthesis of purine nucleosides built on a 3-oxabicyclo[3.2.0]heptane scaffold

Ramon Flores, Albert Rustullet, Ramon Alibés, Angel Álvarez-Larena, Pedro De March, Marta Figueredo, Josep Font

Department of Chemistry

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

33 Citations (Scopus)

Abstract

The photochemical [2 + 2] cycloaddition of chiral 3-chloro and 3-fluoro-5-hydroxymethyl-2(5H)-furanone to ethylene and acetylene has been studied. The effect of the halogen atom on the chemical yield and facial diastereoselectivity of the cycloaddition process has been evaluated. From the major anti cycloadducts, practical syntheses of several purine cyclobutane and cyclobutene-fused nucleosides containing a halogen atom have been developed. The anti-HIV activity of the new nucleoside analogues has been evaluated. © 2011 American Chemical Society.

Original language	English
Pages (from-to)	5369-5383
Journal	Journal of Organic Chemistry
Volume	76
Issue number	13
DOIs	https://doi.org/10.1021/jo200775x
Publication status	Published - 1 Jul 2011

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10.1021/jo200775x

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title = "Synthesis of purine nucleosides built on a 3-oxabicyclo[3.2.0]heptane scaffold",

abstract = "The photochemical [2 + 2] cycloaddition of chiral 3-chloro and 3-fluoro-5-hydroxymethyl-2(5H)-furanone to ethylene and acetylene has been studied. The effect of the halogen atom on the chemical yield and facial diastereoselectivity of the cycloaddition process has been evaluated. From the major anti cycloadducts, practical syntheses of several purine cyclobutane and cyclobutene-fused nucleosides containing a halogen atom have been developed. The anti-HIV activity of the new nucleoside analogues has been evaluated. {\textcopyright} 2011 American Chemical Society.",

author = "Ramon Flores and Albert Rustullet and Ramon Alib{\'e}s and Angel {\'A}lvarez-Larena and March, {Pedro De} and Marta Figueredo and Josep Font",

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T1 - Synthesis of purine nucleosides built on a 3-oxabicyclo[3.2.0]heptane scaffold

AU - Flores, Ramon

AU - Rustullet, Albert

AU - Alibés, Ramon

AU - Álvarez-Larena, Angel

AU - March, Pedro De

AU - Figueredo, Marta

AU - Font, Josep

PY - 2011/7/1

Y1 - 2011/7/1

N2 - The photochemical [2 + 2] cycloaddition of chiral 3-chloro and 3-fluoro-5-hydroxymethyl-2(5H)-furanone to ethylene and acetylene has been studied. The effect of the halogen atom on the chemical yield and facial diastereoselectivity of the cycloaddition process has been evaluated. From the major anti cycloadducts, practical syntheses of several purine cyclobutane and cyclobutene-fused nucleosides containing a halogen atom have been developed. The anti-HIV activity of the new nucleoside analogues has been evaluated. © 2011 American Chemical Society.

AB - The photochemical [2 + 2] cycloaddition of chiral 3-chloro and 3-fluoro-5-hydroxymethyl-2(5H)-furanone to ethylene and acetylene has been studied. The effect of the halogen atom on the chemical yield and facial diastereoselectivity of the cycloaddition process has been evaluated. From the major anti cycloadducts, practical syntheses of several purine cyclobutane and cyclobutene-fused nucleosides containing a halogen atom have been developed. The anti-HIV activity of the new nucleoside analogues has been evaluated. © 2011 American Chemical Society.

U2 - 10.1021/jo200775x

DO - 10.1021/jo200775x

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Synthesis of purine nucleosides built on a 3-oxabicyclo[3.2.0]heptane scaffold

Abstract

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