First enantioselective synthesis of (-)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan |
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Authors: | Yamauchi Satoshi Okazaki Momotoshi Akiyama Koichi Sugahara Takuya Kishida Taro Kashiwagi Takehiro |
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Institution: | Department of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan. syamauch@agr.ehime-u.ac.jp |
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Abstract: | The first highly enantioselective syntheses of tetra-substituted tetrahydrofuran lignan, (-)- and (+)-virgatusin, were achieved. Hemiacetal was stereoselectively obtained from Evans's syn-aldol product as a single isomer. This hemiacetal was converted to (-)-virgatusin via hydrogenolysis. (+)-Virgatusin was also synthesized through the same process. The enantiomeric excess of the both enantiomers was determined as more than 99% ee. |
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