title: Synthesis of (+/-)-brazilin using IBX.
abstract: [reaction: see text] A short synthesis of (+/-)-brazilin is reported. This synthesis uses several interesting and underutilized transformations including a regioselective dirhodium-catalyzed aryl C-H insertion, a regioselective IBX phenol --> o-quinone oxidation, a tautomerization of an o-quinone to a p-quinone methide, and an intramolecular aryl cyclization with a p-quinone methide.
authors.affiliation: Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, USA.
authors.forename: Yaodong
authors.initials: Y
authors.lastname: Huang
authors.forename: Jinsong
authors.initials: J
authors.lastname: Zhang
authors.forename: Thomas R R
authors.initials: TR
authors.lastname: Pettus
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis*; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D011809:Quinones / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D010636:Phenols; D011809:Quinones; D012238:Rhodium; C044362:brazilin