title: Concise synthesis of Obovatol: Chemoselective ortho-bromination of phenol and survey of Cu-catalyzed diaryl ether couplings.
abstract: Concise total synthesis of obovatol (1) was achieved from the commercially available eugenol (5) via linear 4 steps in 40% overall yield. The key features of the synthesis involve the chemoselective orthobromination of phenol in the presence of isolated double bond and the efficient Cu-catalyzed Ullmann coupling of two aromatic moieties for the diaryl ether skeleton.
authors.affiliation: College of Pharmacy, CBITRC, Chungbuk National University, Cheongju, 361-763, Korea.
authors.forename: Jae-Hwan
authors.initials: JH
authors.lastname: Kwak
authors.forename: Jin-Kyung
authors.initials: JK
authors.lastname: In
authors.forename: Mi-Sung
authors.initials: MS
authors.lastname: Lee
authors.forename: Eun-Hwa
authors.initials: EH
authors.lastname: Choi
authors.forename: Heesoon
authors.initials: H
authors.lastname: Lee
authors.forename: Jin Tae
authors.initials: JT
authors.lastname: Hong
authors.forename: Yeo-Pyo
authors.initials: YP
authors.lastname: Yun
authors.forename: Soo Jae
authors.initials: SJ
authors.lastname: Lee
authors.forename: Seung-Yong
authors.initials: SY
authors.lastname: Seo
authors.forename: Young-Ger
authors.initials: YG
authors.lastname: Suh
authors.forename: Jae-Kyung
authors.initials: JK
authors.lastname: Jung
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D001713:Biphenyl Compounds / Q000138:chemical synthesis*; D001966:Bromine / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004987:Ethers; D008024:Ligands; D010636:Phenols / Q000737:chemistry*; D010647:Phenyl Ethers / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000475:Alkenes; D000890:Anti-Infective Agents; D001713:Biphenyl Compounds; D004987:Ethers; D008024:Ligands; D010636:Phenols; D010647:Phenyl Ethers; D003300:Copper; C036795:obovatol; D001966:Bromine