title: Total synthesis of brazilin.
abstract: Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.
authors.affiliation: College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University , 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea.
authors.forename: Youngeun
authors.initials: Y
authors.lastname: Jung
authors.forename: Ikyon
authors.initials: I
authors.lastname: Kim
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001578:Benzopyrans; D007204:Indium; C044362:brazilin