Issue 27, 2014

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
11 ⵎⴰⵕ 2014
Accepted
20 ⵎⴰⵢ 2014
First published
21 ⵎⴰⵢ 2014

Org. Biomol. Chem., 2014,12, 4879-4884

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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