title: Total synthesis of A-315675: a potent inhibitor of influenza neuraminidase.
abstract: A concise, stereocontrolled, and practical synthesis of a neuraminidase inhibitor consisting of a highly functionalized D-proline scaffold is described. Key features involve a stereocontrolled addition of a propiolate ester to a chiral nonracemic nitrone derived originally from D-serine and the manipulation of acyclic and cyclic motifs en route to the target in 12.8% overall yield over 22 steps. Several crystalline intermediates were suitable for single-crystal X-ray analysis.
authors.affiliation: Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, Québec H3C 3J7, Canada. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Malken
authors.initials: M
authors.lastname: Bayrakdarian
authors.forename: Xuehong
authors.initials: X
authors.lastname: Luo
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry*; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000201:enzymology; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C456059:A 315675; D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D011759:Pyrrolidines; D009439:Neuraminidase