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 мар 2014
Accepted
20 май 2014
First published
21 май 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements