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https://hdl.handle.net/10356/103102| Title: | A total synthesis of (+)-negamycin through isoxazolidine allylation | Authors: | Bates, Roderick Wayland Khanizeman, Rab'iah Nisha Hirao, Hajime Tay, Yu Shan Sae-Lao, Patcharaporn |
Keywords: | Science::Chemistry::Organic chemistry::Organic synthesis | Issue Date: | 2014 | Source: | 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. | Journal: | Organic & Biomolecular Chemistry | Series/Report no.: | Organic & biomolecular chemistry | 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. | URI: | https://hdl.handle.net/10356/103102 http://hdl.handle.net/10220/24385 |
ISSN: | 1477-0520 | DOI: | 10.1039/c4ob00537f | Schools: | School of Physical and Mathematical Sciences | Rights: | © 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]. | Fulltext Permission: | open | Fulltext Availability: | With Fulltext |
| Appears in Collections: | SPMS Journal Articles |
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| File | Description | Size | Format | |
|---|---|---|---|---|
| A Total Synthesis of (+)-Negamycin through Isoxazolidine Allylation.pdf | Main article | 371.72 kB | Adobe PDF |  View/Open |
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