A total synthesis of (+)-negamycin through isoxazolidine allylation
Bates, Roderick W.
Khanizeman, Rab'iah Nisha
Tay, Yu Shan
Date of Issue2014
School of Physical and Mathematical Sciences
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.
DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
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].