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

Roderick W. Bates; Rab'Iah Nisha Khanizeman; Hajime Hirao; Yu Shan Tay; Patcharaporn Sae-Lao

doi:10.1039/c4ob00537f

Author(s)

Roderick W. Bates
Rab'Iah Nisha Khanizeman
Hajime Hirao
Yu Shan Tay
Patcharaporn Sae-Lao

Detail(s)

Original language	English
Pages (from-to)	4879-4884
Journal / Publication	Organic and Biomolecular Chemistry
Volume	12
Issue number	27
Publication status	Published - 21 Jul 2014
Externally published	Yes

Link(s)

DOI	DOI https://doi.org/10.1039/c4ob00537f Final Published version
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Link to Scopus	https://www.scopus.com/record/display.uri?eid=2-s2.0-84902792288&origin=recordpage
Permanent Link	https://scholars.cityu.edu.hk/en/publications/publication(e1d35976-6629-4413-b391-54d6dd52a2b0).html

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. This journal is © the Partner Organisations 2014.

Citation Format(s)

[ RIS ] [ BibTeX ]

A total synthesis of (+)-negamycin through isoxazolidine allylation. / Bates, Roderick W.; Khanizeman, Rab'Iah Nisha; Hirao, Hajime et al.
In: Organic and Biomolecular Chemistry, Vol. 12, No. 27, 21.07.2014, p. 4879-4884.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

Bates, RW, Khanizeman, RIN, Hirao, H, Tay, YS & Sae-Lao, P 2014, 'A total synthesis of (+)-negamycin through isoxazolidine allylation', Organic and Biomolecular Chemistry, vol. 12, no. 27, pp. 4879-4884. https://doi.org/10.1039/c4ob00537f

Bates, R. W., Khanizeman, RI. N., Hirao, H., Tay, Y. S., & Sae-Lao, P. (2014). A total synthesis of (+)-negamycin through isoxazolidine allylation. Organic and Biomolecular Chemistry, 12(27), 4879-4884. https://doi.org/10.1039/c4ob00537f

Bates RW, Khanizeman RIN, Hirao H, Tay YS, Sae-Lao P. A total synthesis of (+)-negamycin through isoxazolidine allylation. Organic and Biomolecular Chemistry. 2014 Jul 21;12(27):4879-4884. doi: 10.1039/c4ob00537f

Bates, Roderick W. ; Khanizeman, Rab'Iah Nisha ; Hirao, Hajime et al. / A total synthesis of (+)-negamycin through isoxazolidine allylation. In: Organic and Biomolecular Chemistry. 2014 ; Vol. 12, No. 27. pp. 4879-4884.