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Diastereoselective Synthesis of a Precursor of Homocarbocyclic Nucleosides

✍ Scribed by Carmen M. Gonzalez-Alvarez; Leticia Quintero; Fernando Santiesteban; Jean-Louis Fourrey

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
184 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

A convenient diastereoselective synthesis of an immediate high yielding new type of Pd(0) catalyzed cyclization of a suitable hydrazine derivative together with a stereospecific precursor for a rapid access to a variety of homo-carbocyclic nucleosides, is described. The synthetic scheme involves a OsO 4 triggered dihydroxylation step. synthesis of a functionalized cyclopentylamine which is

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Anomeric αand β-N,O-psiconucleosides were prepared by 1,3-dipolar cycloaddition of C-ethoxycarbonyl N-methyl nitrone with ethyl 2-acetyloxyacrylate, followed by Vorbrüggen nucleosidation. The synthetic scheme has been applied to all purine and pyrimidine nucleobases. Nucleosidation can proceed under