Synthesis of (+/-)-brazilin using IBX.
[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.
Huang
Yaodong
Y
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, USA.
Zhang
Jinsong
J
Pettus
Thomas R R
TR
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
D001578:Benzopyrans; D010636:Phenols; D011809:Quinones; D012238:Rhodium; C044362:brazilin