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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.
ISSN: 1477-0520
DOI: 10.1039/c4ob00537f
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:].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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