A total synthesis of (+)-negamycin through isoxazolidine allylationElectronic supplementary information (ESI) available: Copies of 1H and 13C NMR spectra and computational details. See DOI: 10.1039/c4ob00537f

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. The β-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate.