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Synthesis 1997; 1997(7): 783-786
DOI: 10.1055/s-1997-1419
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The Synthesis of Conformationally Restricted Analogs of Acetolactate

William A. Kleschick* , Liying S. Lu, Scott Thornburgh
  • *DowElanco Research Laboratory, 9330 Zionsville Road, Bldg. 306/B1, Indianapolis, IN 46268-1054, USA, Fax +1(317)3373252; E-mail: wakleschick@dowelanco.com
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Publication Date:
31 December 2000 (online)

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The synthesis of a conformationally restricted analog of acetolactate 1, a natural substrate for ketol acid reductoisomerase, is described. The key features of the successful synthesis are epoxidation of unsaturated ester 10 using urea-hydrogen peroxide complex and subsequent rearrangement of epoxide 11 to allylic alcohol 13 with aluminum tri-tert-butoxide. Compound 1 was neither a substrate for ketol acid reductoisomerase nor an inhibitor of the enzyme at concentrations up to 50 ppm.

acetolactate - ketol-acid reductoisomerase (EC 1.1.1.86) - aluminum tri-tert-butoxide - epoxidation - urea-hydrogen peroxide

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