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

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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

© Georg Thieme Verlag Stuttgart

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

ISSN

0936-5214

Language

  • en