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

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

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

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

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

Original language	English
Pages (from-to)	4879-4884
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	27
DOIs	https://doi.org/10.1039/c4ob00537f
Publication status	Published - Jul 21 2014
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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. This journal is",

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AU - Hirao, Hajime

AU - Tay, Yu Shan

AU - Sae-Lao, Patcharaporn

PY - 2014/7/21

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

Abstract

ASJC Scopus Subject Areas

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