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

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

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 a...

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Main Authors: Bates, Roderick Wayland, Khanizeman, Rab'iah Nisha, Hirao, Hajime, Tay, Yu Shan, Sae-Lao, Patcharaporn
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
Science::Chemistry::Organic chemistry::Organic synthesis
Online Access:https://hdl.handle.net/10356/103102
http://hdl.handle.net/10220/24385
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1031022023-02-28T19:42:42Z A total synthesis of (+)-negamycin through isoxazolidine allylation Bates, Roderick Wayland Khanizeman, Rab'iah Nisha Hirao, Hajime Tay, Yu Shan Sae-Lao, Patcharaporn School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry::Organic synthesis 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. Accepted version 2014-12-09T06:13:13Z 2019-12-06T21:05:39Z 2014-12-09T06:13:13Z 2019-12-06T21:05:39Z 2014 2014 Journal Article Bates, R. W., Khanizeman, R. N., Hirao, H., Tay, Y. S., & Sae-Lao, P. (2014). A total synthesis of (+)-negamycin through isoxazolidine allylation. Organic & Biomolecular Chemistry, 12(27), 4879-4884. 1477-0520 https://hdl.handle.net/10356/103102 http://hdl.handle.net/10220/24385 10.1039/c4ob00537f en Organic & Biomolecular Chemistry Organic & biomolecular chemistry © 2014 Royal Society of Chemistry. This is the author created version of a work that has been peer reviewed and accepted for publication by Organic & Biomolecular Chemistry, The Royal Society of Chemistry. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [Article DOI: http://dx.doi.org/10.1039/c4ob00537f]. 6 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry::Organic chemistry::Organic synthesis
spellingShingle Science::Chemistry::Organic chemistry::Organic synthesis
Bates, Roderick Wayland
Khanizeman, Rab'iah Nisha
Hirao, Hajime
Tay, Yu Shan
Sae-Lao, Patcharaporn
A total synthesis of (+)-negamycin through isoxazolidine allylation
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Bates, Roderick Wayland
Khanizeman, Rab'iah Nisha
Hirao, Hajime
Tay, Yu Shan
Sae-Lao, Patcharaporn
format Article
author Bates, Roderick Wayland
Khanizeman, Rab'iah Nisha
Hirao, Hajime
Tay, Yu Shan
Sae-Lao, Patcharaporn
author_sort Bates, Roderick Wayland
title A total synthesis of (+)-negamycin through isoxazolidine allylation
title_short A total synthesis of (+)-negamycin through isoxazolidine allylation
title_full A total synthesis of (+)-negamycin through isoxazolidine allylation
title_fullStr A total synthesis of (+)-negamycin through isoxazolidine allylation
title_full_unstemmed A total synthesis of (+)-negamycin through isoxazolidine allylation
title_sort total synthesis of (+)-negamycin through isoxazolidine allylation
publishDate 2014
url https://hdl.handle.net/10356/103102
http://hdl.handle.net/10220/24385
_version_ 1759854810385874944

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