The nitrile oxide cycloaddition (NOC) route to a multipurpose C-nucleoside intermediate

A new class of C-nucleosides [6]

Alan P. Kozikowski, Steven Goldstein

Research output: Contribution to journalArticle

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-O 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
StatePublished - 1983
Externally publishedYes

Fingerprint

Nitriles
Cycloaddition
Nucleosides
Oxides
Isoxazoles
Nucleophiles
Antiviral Agents
Esters
Anti-Bacterial Agents
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

The nitrile oxide cycloaddition (NOC) route to a multipurpose C-nucleoside intermediate : A new class of C-nucleosides [6]. / Kozikowski, Alan P.; Goldstein, Steven.

In: Journal of Organic Chemistry, Vol. 48, No. 7, 1983, p. 1139-1141.

Research output: Contribution to journalArticle

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