title: A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation.
abstract: A short synthetic route to the trimethyl ether of brazilin was developed in 6 steps from 7-methoxychromene with 78% overall yield. Regioselective installation of a formyl group onto 7-methoxychromene followed by reduction and acetylation afforded allylic acetate. Palladium-catalyzed allylic coupling of allylic acetate with arylboronic acid provided direct access to 3-benzylchromene which was converted to the target molecule upon ensuing dihydroxylation and acid-catalyzed cyclization in a highly concise manner.
authors.affiliation: College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea. ikyonkim@yonsei.ac.kr.
authors.forename: Youngeun
authors.initials: Y
authors.lastname: Jung
authors.forename: Ikyon
authors.initials: I
authors.lastname: Kim
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D010165:Palladium / Q000737:chemistry*
chemical_list: D000085:Acetates; D000498:Allyl Compounds; D001578:Benzopyrans; D010165:Palladium; C498551:allyl acetate; C044362:brazilin