Concise synthesis of Obovatol: Chemoselective ortho-bromination of phenol and survey of Cu-catalyzed diaryl ether couplings.
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.
Kwak
Jae-Hwan
JH
College of Pharmacy, CBITRC, Chungbuk National University, Cheongju, 361-763, Korea.
In
Jin-Kyung
JK
Lee
Mi-Sung
MS
Choi
Eun-Hwa
EH
Lee
Heesoon
H
Hong
Jin Tae
JT
Yun
Yeo-Pyo
YP
Lee
Soo Jae
SJ
Seo
Seung-Yong
SY
Suh
Young-Ger
YG
Jung
Jae-Kyung
JK
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
D000475:Alkenes; D000890:Anti-Infective Agents; D001713:Biphenyl Compounds; D004987:Ethers; D008024:Ligands; D010636:Phenols; D010647:Phenyl Ethers; D003300:Copper; C036795:obovatol; D001966:Bromine