Use of the Benzyl Mesylate for the Synthesis of Tetrahydrofuran Lignan: Syntheses of 7,8-trans, 7′,8′-trans, 7,7′-cis, and 8,8′-cis-Virgatusin Stereoisomers
Bioscience Biotechnology and Biochemistry2007Vol. 71(9), pp. 2248–2255
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Satoshi Yamauchi, Tomofumi Nakato, Masahiro Tsuchiya, Koichi Akiyama, Masafumi Maruyama, Takuya Sugahara, Taro Kishida
Abstract
The benzyl mesylate was employed to construct the tetrasubstituted tetrahydrofuran lignan with avoiding Friedel-Crafts type of reaction. The optically pure 7,8trans, 7 0 ,8 0 -trans, 7,7 0 -cis, and 8,8 0 -cis-virgatusin stereoisomers were synthesized. The enantiomeric excess was 99%.
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