The synthesis of conformationally restricted analogs of acetolactate

Article abstract of DOI:10.1055/s-1997-1419

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.