title: 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).
abstract: 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.
authors: College of Pharmacy, The University of Georgia, Athens, GA 30602, USA.
authors: Yun H
authors: YH
authors: Jin
authors: Peng
authors: P
authors: Liu
authors: Jianing
authors: J
authors: Wang
authors: Udayan
authors: U
authors: Das
authors: Robert
authors: R
authors: Baker
authors: John
authors: J
authors: Huggins
authors: Chung K
authors: CK
authors: Chu
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D018155:Orthopoxvirus / Q000187:drug effects*
chemical_list: D000998:Antiviral Agents; D003517:Cyclopentanes; D009705:Nucleosides; C013905:cyclopentenone