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Issue 27, 2014
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A total synthesis of (+)-negamycin through isoxazolidine allylation

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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.

Graphical abstract: A total synthesis of (+)-negamycin through isoxazolidine allylation

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Publication details

The article was received on 11 Mar 2014, accepted on 20 May 2014 and first published on 21 May 2014


Article type: Paper
DOI: 10.1039/C4OB00537F
Citation: Org. Biomol. Chem., 2014,12, 4879-4884
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    A total synthesis of (+)-negamycin through isoxazolidine allylation

    R. W. Bates, R. N. Khanizeman, H. Hirao, Y. S. Tay and P. Sae-Lao, Org. Biomol. Chem., 2014, 12, 4879
    DOI: 10.1039/C4OB00537F

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