Cortés Manuel J, Armstrong Veronica, Barrero Alejandro F, Bandoni Arnaldo E, Priestap Horacio A, Fournet Alain, Prina Eric
Depto. Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla, 306, Santiago 22, Chile.
Nat Prod Res. 2006 Sep;20(11):1008-14. doi: 10.1080/14786410600921391.
Epoxidation of argentilactone (1) with m-chloroperbenzoic acid gave a diasteromeric mixture of 2 and 3 in a ratio 1.8 : 1, with total yield 60%. The configuration of 7,8-oxirane ring for both diasteromers was determined by NMR analysis. Reaction of 1 with urea hydrogen peroxide gave the 3,4-epoxide (4) in 65% yield. The in vitro activity of 2, 3, 4 and argentilactone against Leishmania amazonensis was tested, only epoxides (2) and (3) showed leishmanicidal effect.
