Baeyer-Villiger oxidation promoted by reaction of peracids with cyclic oxocarbenium ions generated in situ from internal hemiketals.
[reaction: see text] Reactive cyclic oxocarbenium ions, generated in situ from internal hemiketals, undergo Baeyer-Villiger oxidation upon exposure to m-chloroperbenzoic acid leading, after hydrolysis of the resultant lactones, to acyclic fragments for use in natural product synthesis.
Hunt
K W
KW
Department of Chemistry and Biochemistry, Montana State University, Bozeman 59717, USA.
Grieco
P A
PA
D007659:Ketones / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D017382:Reactive Oxygen Species; D013256:Steroids / Q000737:chemistry
D007659:Ketones; D018942:Macrolides; D017382:Reactive Oxygen Species; D013256:Steroids