Forming spirocyclohexadienone-oxocarbenium cation species in the biomimetic synthesis of amomols.
The oxidation of appropriate 2-(4-hydroxyphenyl)ethyl ketones gives direct access to amomols by means of the formation of a transient spirocyclohexadienone-oxocarbenium ion that is intermolecularly intercepted by an alcohol. Furthermore, homochiral amomols and other new analogues were synthesized for the first time and were biologically evaluated on Plasmodium falciparum.
Département de Pharmacochimie Moléculaire, Université Joseph Fourier-Grenoble 1, CNRS UMR 5063, CNRS ICMG FR 2607, bâtiment André Rassat, 470 rue de la Chimie, F-38041 Grenoble Cedex 9, France.
Mariam
M
Traoré
Marjorie
M
Maynadier
Florence
F
Souard
Luc
L
Choisnard
Henri
H
Vial
Yung-Sing
YS
Wong
D032701:Biomimetics; D002412:Cations / Q000737:chemistry / Q000378:metabolism; D003510:Cyclohexanes / Q000737:chemistry* / Q000378:metabolism; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007659:Ketones / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010963:Plasmodium falciparum / Q000737:chemistry / Q000378:metabolism; D013141:Spiro Compounds / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism
D002412:Cations; D003510:Cyclohexanes; D005663:Furans; D007659:Ketones; D013141:Spiro Compounds