THE SYNTHESIS OF CONFORMATIONALLY RESTRICTED ANALOGS OF ACETOLACTATE

Authors
KLESCHICK WA LU LS THRONBURGH S
Citation
Wa. Kleschick et al., THE SYNTHESIS OF CONFORMATIONALLY RESTRICTED ANALOGS OF ACETOLACTATE, Synthesis, (7), 1997, pp. 783
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
7
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):7<783:TSOCRA>2.0.ZU;2-M
Abstract
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 unsatu rated ester 10 using urea-hydrogen peroxide complex and subsequent rea rrangement of epoxide 11 to allylic alcohol 13 with aluminum tri-tert- butoxide. Compound 1 was neither a substrate for ketol acid reductoiso merase nor an inhibitor of the enzyme at concentrations up to 50 ppm.