Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones.
Manganese(III)-mediated oxidative transformations of dearomatized phloroglucinol (1,3,5-trihydroxybenzene) derivatives are reported. A number of cyclization modes have been observed, including polycyclization to afford bicyclo[2.2.2]octadiones via a formal oxidative radical [4 + 2] cycloaddition.
Department of Chemistry and Center for Chemical Methodology and Library, Development, Boston University, Boston, Massachusetts 02215, USA.
Branko
B
Mitasev
John A
JA
Porco
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008345:Manganese / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry*
D001643:Bridged Bicyclo Compounds; D007659:Ketones; D008345:Manganese; D010696:Phloroglucinol