Bicyclic Nucleoside Synthesis-A Photochemical Approach

The synthesis of a series of bicyclic nucleosides using photolytic ring-expansion of cyclobutanones is reported. The cyclobutanone precursors were prepared by [2+2] cycloaddition of a series of cyclic alkenes with chlorinated ketenes, derived from dichloro- and trichloroacetyl chloride. The synthesi...

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Published inNucleosides, nucleotides & nucleic acids Vol. 27; no. 5; pp. 484 - 494
Main Authors Lee-Ruff, E., Wells, D.
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.05.2008
Taylor & Francis
Subjects
Bicyclic nucleosides
Biochemistry & Molecular Biology
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Drug Design
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Nucleosides - chemical synthesis
Nucleosides - chemistry
Photochemistry
Photolysis
ring-expansion
Science & Technology
Stereoisomerism
synthesis
synthesis
FURANOSE RING
NUCLEIC-ACID
ANALOGS
photolysis
ring-expansion
DNA
bicyclic nucleosides
PRINCIPLES
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Summary:The synthesis of a series of bicyclic nucleosides using photolytic ring-expansion of cyclobutanones is reported. The cyclobutanone precursors were prepared by [2+2] cycloaddition of a series of cyclic alkenes with chlorinated ketenes, derived from dichloro- and trichloroacetyl chloride. The synthesis of the nucleosides was achieved through photolysis of cyclobutanone precursors with 6-chloropurine by UV irradiation. The generality of this method was investigated and the absolute stereochemistry was assigned by NMR spectroscopy. The photoproducts demonstrated a marked preference for the 2′-exo conformation.
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ISSN:1525-7770
1532-2335
DOI:10.1080/15257770802088886