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

Alan P. Kozikowski; Steven Goldstein

doi:10.1021/jo00155a054

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 journal › Article › peer-review

33 Scopus citations

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 language	English (US)
Pages (from-to)	1139-1141
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	48
Issue number	7
DOIs	https://doi.org/10.1021/jo00155a054
State	Published - Apr 1983
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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.",

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AB - 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.

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

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