The Nitrlle Oxide Cycloaddition (NOC) Route to a Multipurpose C-Nucleoside Intermediate: A New Class of C-Nucleosides

Alan P. Kozikowski, Steven Goldstein

Research output: Contribution to journalArticlepeer-review

Abstract

A new route to the important class of antibiotic and antiviral agents, the C-nucleosides, has been developed. The nitrile oxide generated from a protected derivative of β-D-ribofuranosylnitromethane has been shown to react with ethoxyacetylene to deliver an isoxazole C-nucleoside. On hydrogenolytic cleavage of the N-0 bond, a β-keto ester is formed that can be reacted with a bis-nucleophile to yield a new C-nucleoside analogue.

Original languageEnglish (US)
Pages (from-to)1139-1141
Number of pages3
JournalJournal of Organic Chemistry
Volume48
Issue number7
DOIs
StatePublished - Apr 1983

ASJC Scopus subject areas

  • Organic Chemistry

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