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Published on: August 16, 2018
Synthesis of Phenol-Derived cis-Vinyl Ethers Using Ethynyl Benziodoxolone
Tomoki Ura1, Daisuke Shimbo1, Masaharu Yudasaka1
1Laboratory of Pharmaceutical Synthetic Chemistry, Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu, 501-1196, Japan.
Abstract:
The stereoselective synthesis of cis-β-phenoxyvinyl benziodoxolones (cis-β-phenol-VBXs) from an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) and various phenols is reported herein. The reaction tolerates different phenol derivatives, including complex natural products, and can be conducted under mild conditions. The synthesis was performed in an aqueous solvent in the absence and presence of a catalytic amount of a base. Selectively mono- and di-deuterated cis-β-phenol-VBXs were also prepared. cis-β-Phenol-VBXs were stereospecifically derivatized to cis-alkynylvinyl ethers and cis-iodovinyl ethers without loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.
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