Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization.
An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, USA.
Jianglong
J
Zhu
Nicholas P
NP
Grigoriadis
Jonathan P
JP
Lee
John A
JA
Porco
D001578:Benzopyrans / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010860:Pigments, Biological / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D001578:Benzopyrans; D008024:Ligands; D010860:Pigments, Biological; D012997:Solvents; C494154:azaphilone; D003300:Copper