Total synthesis of (+/-)-mitorubrinic acid.
[reaction: see text] (+/-)-Mitorubrinic acid, a member of the azaphilone family of natural products, has been constructed in 12 steps. Key aspects of the synthesis include elaboration and oxidative dearomatization of an isocoumarin intermediate to provide the azaphilone nucleus with a disubstituted, unsaturated carboxylic acid side chain.
Marsini
Maurice A
MA
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106, USA.
Gowin
Kristoffer M
KM
Pettus
Thomas R R
TR
D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism
D001565:Benzoates; D002264:Carboxylic Acids; C433878:mitorubrinic acid