Synthesis of Purine Nucleosides Built on a 3-Oxabicyclo[3.2.0]heptane Scaffold

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...

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Veröffentlicht in:	Journal of organic chemistry 2011-07, Vol.76 (13), p.5369-5383
Hauptverfasser:	Flores, Ramon, Rustullet, Albert, Alibés, Ramon, Álvarez-Larena, Angel, March, Pedro de, Figueredo, Marta, Font, Josep
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Bridged Bicyclo Compounds - chemistry Carbohydrates. Nucleosides and nucleotides Chemistry Crystallography, X-Ray Cycloheptanes - chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Medical sciences Models, Molecular Molecular Structure Nucleosides - chemical synthesis Nucleosides - chemistry Nucleosides, nucleotides and oligonucleotides Organic chemistry Pharmacology. Drug treatments Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Preparations and properties Purines - chemical synthesis Purines - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo200775x