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 YAMAUCHI; Tomofumi NAKATO; Masahiro TSUCHIYA; Koichi AKIYAMA; Masafumi MARUYAMA; Takuya SUGAHARA; Taro KISHIDA

doi:10.1271/bbb.70236

Organic Chemistry Regular Papers

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 YAMAUCHI, Tomofumi NAKATO, Masahiro TSUCHIYA, Koichi AKIYAMA, Masafumi MARUYAMA, Takuya SUGAHARA, Taro KISHIDA

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Keywords: lignan, virgatusin, tetrahydrofuran lignan

JOURNAL FREE ACCESS

2007 Volume 71 Issue 9 Pages 2248-2255

DOI https://doi.org/10.1271/bbb.70236

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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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