Details

Autor(en) / Beteiligte

• Jin, Yun H
• Liu, Peng
• Wang, Jianing
• Baker, Robert
• Huggins, John
• Chu, Chung K

Titel

Practical Synthesis of d- and l-2-Cyclopentenone and Their Utility for the Synthesis of Carbocyclic Antiviral Nucleosides against Orthopox Viruses (Smallpox, Monkeypox, and Cowpox Virus)

Ist Teil von

• Journal of organic chemistry, 2003-11, Vol.68 (23), p.9012-9018

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2003

Quelle

MEDLINE

Beschreibungen/Notizen

• Highly efficient and practical methodology for the syntheses of d- and l-4,5-O-isopropylidene-2-cyclopentenone (9 and 22), versatile intermediates for the synthesis of carbocyclic nucleosides, have been developed via a ring-closing metathesis reaction from d-ribose in eight steps. The utility of d- and l-4,5-O-isopropylidene-2-cyclopentenone is demonstrated by their application for the preparation of d-cyclopentyl-6-azauridine 12 and d-cyclopentenyl-5-halocytosine nucleosides (33−35) using Mitsunobu reaction to introduce pyrimidine bases as potential antiviral agents. Preliminary antiviral activity against orthopox viruses (smallpox, monkeypox, and cowpox virus) of the synthesized nucleosides are described.