Data di Pubblicazione:
2018
Citazione:
Chemoenzymatic Synthesis of Luliconazole Mediated by Lipases / T.D.S. Fonseca, L.D. Lima, M.D.C.F. de Oliveira, T.L.G. de Lemos, D. Zampieri, F.E. Molinari, M.C. de Mattos. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 18(2018 May 15), pp. 2110-2116. [10.1002/ejoc.201800250]
Abstract:
A straightforward chemoenzymatic synthesis of luli- conazole has been developed. The key step involved the preparation of the enantiomerically pure beta-halohydrin (1S)-2-chloro- 1-(2,4-dichlorophenyl)-1-ethanol through kinetic resolution of the corresponding racemic acetate. This was achieved by a hydrolytic approach, mediated by the lipase from Thermomyces lanuginosus or Novozym 435®. The latter enzyme proved to be a robust biocatalyst for the kinetic resolution, and the halohydrin was obtained with high selectivity (ee > 99%, E > 200) after just 15 min, at 45 °C. It could be reused five times with maintenance of high values of both conversion and enantioselectivity. Subsequently, the (S)-beta-halohydrin was sub- jected to a mesylation reaction; the mesylated derivative re- acted with 1-cyanomethylimidazole in the presence of CS2 to give luliconazole in 43 % yield with >99 % ee.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
biocatalysis; chemoenzymatic synthesis; stereoselectivity; enzymatic reaction
Elenco autori:
T.D.S. Fonseca, L.D. Lima, M.D.C.F. de Oliveira, T.L.G. de Lemos, D. Zampieri, F.E. Molinari, M.C. de Mattos
Link alla scheda completa: