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

Satoshi YAMAUCHIFaculty of Agriculture, Ehime University

Tomofumi NAKATOFaculty of Agriculture, Ehime University

Masahiro TSUCHIYAFaculty of Agriculture, Ehime University

Koichi AKIYAMAIntegrated Center for Sciences, Tarumi Station, Ehime University

Masafumi MARUYAMAFaculty of Agriculture, Ehime University

Takuya SUGAHARAFaculty of Agriculture, Ehime University

Taro KISHIDAFaculty of Agriculture, Ehime University

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Abstract

The benzyl mesylate was employed to construct the tetrasubstituted tetrahydrofuran lignan with avoiding Friedel-Crafts type of reaction. The optically pure 7,8-trans, 7′,8′-trans, 7,7′-cis, and 8,8′-cis-virgatusin stereoisomers were synthesized. The enantiomeric excess was >>99%.

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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

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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

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