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

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

18 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 © the Partner Organisations 2014.

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

Access Output

10.1039/c4ob00537f

Other Access Options

Check CityUHK Library

Permanent Link

Right click to copy link

Cite this

@article{e1d3597666294413b39154d6dd52a2b0,

title = "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. This journal is {\textcopyright} the Partner Organisations 2014.",

author = "Bates, {Roderick W.} and Khanizeman, {Rab'Iah Nisha} and Hajime Hirao and Tay, {Yu Shan} and Patcharaporn Sae-Lao",

year = "2014",

month = jul,

day = "21",

doi = "10.1039/c4ob00537f",

language = "English",

volume = "12",

pages = "4879--4884",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "27",

}

TY - JOUR

T1 - A total synthesis of (+)-negamycin through isoxazolidine allylation

AU - Bates, Roderick W.

AU - Khanizeman, Rab'Iah Nisha

AU - Hirao, Hajime

AU - Tay, Yu Shan

AU - Sae-Lao, Patcharaporn

PY - 2014/7/21

Y1 - 2014/7/21

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84902792288&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-84902792288&origin=recordpage

U2 - 10.1039/c4ob00537f

DO - 10.1039/c4ob00537f

M3 - RGC 21 - Publication in refereed journal

C2 - 24875354

SN - 1477-0520

VL - 12

SP - 4879

EP - 4884

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 27

ER -

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

Abstract

Access Output

Other Access Options

Permanent Link

Other Files and Links

Fingerprint

Cite this