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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkenes / chemistry
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Anti-Infective Agents / chemical synthesis*
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Biphenyl Compounds / chemical synthesis*
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Bromine / chemistry*
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Catalysis
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Copper / chemistry*
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Ethers
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Ligands
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Phenols / chemistry*
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Phenyl Ethers / chemical synthesis*
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Spectrophotometry, Infrared
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Spectroscopy, Fourier Transform Infrared
Substances
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Alkenes
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Anti-Infective Agents
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Biphenyl Compounds
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Ethers
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Ligands
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Phenols
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Phenyl Ethers
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Copper
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obovatol
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Bromine