Synthesis p. 783 - 786 (1997)
Update date:2022-08-03
Topics:
Kleschick, William A.
Lu, Liying S.
Thornburgh, Scott
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 II 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.
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