title: Total Synthesis of Anti-Influenza Agents Zanamivir and Zanaphosphor via Asymmetric Aza-Henry Reaction.
abstract: The potent anti-influenza agents, zanamivir and its phosphonate congener, are synthesized by using a nitro group as the latent amino group at C4 for asymmetric aza-Henry reaction with a chiral sulfinylimine, which is derived from inexpensive d-glucono-δ-lactone to establish the essential nitrogen-containing substituent at C5. This method provides an efficient way to construct the densely substituted dihydropyran core of zanamivir and zanaphosphor without using the hazardous azide reagent.
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei 106, Taiwan.
authors.forename: Long-Zhi
authors.initials: LZ
authors.lastname: Lin
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei 106, Taiwan.|The Genomics Research Center, Academia Sinica , Taipei 115, Taiwan.
authors.forename: Jim-Min
authors.initials: JM
authors.lastname: Fang
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007251:Influenza, Human / Q000188:drug therapy*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009975:Orthomyxoviridae / Q000187:drug effects*; D053243:Zanamivir / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000998:Antiviral Agents; D001372:Aza Compounds; D053243:Zanamivir