A rapid and highly diastereoselective synthesis of enantiomerically pure (4R,5R)- and (4S,5S)-isocytoxazone

Buckley, Benjamin; Page, Philip C. Bulman; McKee, Vickie

A rapid and highly diastereoselective synthesis of enantiomerically pure (4R,5R)- and (4S,5S)-isocytoxazone

journal contribution

posted on 2013-11-18, 14:43 authored by Benjamin BuckleyBenjamin Buckley, Philip C. Bulman Page, Vickie McKee

A three-step protocol for the highly diastereoselective (>98%) synthesis of both (4R,5R)- and (4S,5S)-isocytoxazone from d- or l-tyrosine is reported. The diastereoselection was confirmed by X-ray crystallography. This synthesis is currently the highest yielding approach towards these enantiomerically pure biologically active oxazolidinones.

History

School

Science

Department

Chemistry

Citation

BUCKLEY, B.R., PAGE, P.C.B. and MCKEE, V., 2011. A rapid and highly diastereoselective synthesis of enantiomerically pure (4R,5R)- and (4S,5S)-isocytoxazone. Synlett, 10, pp. 1399 - 1402.

Publisher

Version

AM (Accepted Manuscript)

Publication date

2011

Notes

This article was published in the journal Synlett [© Georg Thieme Verlag Stuttgart]. The definitive version is available at: http://dx.doi.org/10.1055/s-0030-1260561