title: A total synthesis of (+)-negamycin through isoxazolidine allylation.
abstract: The β-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate. The key allylation reaction proceeded with complete trans-selectivity, which is attributed to electrostatic attraction between the chlorine atom and the iminium ion in the Sakurai intermediate.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore637371. roderick@ntu.edu.sg.
authors.forename: Roderick W
authors.initials: RW
authors.lastname: Bates
authors.forename: Rab'iah Nisha
authors.initials: RN
authors.lastname: Khanizeman
authors.forename: Hajime
authors.initials: H
authors.lastname: Hirao
authors.forename: Yu Shan
authors.initials: YS
authors.lastname: Tay
authors.forename: Patcharaporn
authors.initials: P
authors.lastname: Sae-Lao
mesh_terms: D000599:Amino Acids, Diamino / Q000138:chemical synthesis; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D007555:Isoxazoles / Q000737:chemistry*; D055672:Static Electricity
chemical_list: D000599:Amino Acids, Diamino; D000900:Anti-Bacterial Agents; D007555:Isoxazoles; C100200:negamycin