First enantioselective synthesis of (−)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan

Satoshi Yamauchi; Momotoshi Okazaki; Koichi Akiyama; Takuya Sugahara; Taro Kishida; Takehiro Kashiwagi

doi:10.1039/B501151E

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First enantioselective synthesis of (−)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan

Satoshi Yamauchi,*^a Momotoshi Okazaki,^a Koichi Akiyama,^b Takuya Sugahara,^a Taro Kishida^a and Takehiro Kashiwagi^a

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* Corresponding authors

^a Department of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime, Japan
E-mail: syamauch@agr.ehime-u.ac.jp
Fax: +81-89-977-4364

^b Integrated Center for Sciences Tarumi Station, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime, Japan

Abstract

The first highly enantioselective syntheses of tetra-substituted tetrahydrofuran lignan, (−)- and (+)-virgatusin, were achieved. Hemiacetal 15 was stereoselectively obtained from Evans's syn-aldol product 8 as a single isomer. This hemiacetal 15 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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Article information

DOI: https://doi.org/10.1039/B501151E
Article type: Paper
Submitted: 24 Jan 2005
Accepted: 09 Mar 2005
First published: 24 Mar 2005

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Org. Biomol. Chem., 2005,3, 1670-1675

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First enantioselective synthesis of (−)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan

S. Yamauchi, M. Okazaki, K. Akiyama, T. Sugahara, T. Kishida and T. Kashiwagi, Org. Biomol. Chem., 2005, 3, 1670 DOI: 10.1039/B501151E

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Organic & Biomolecular Chemistry

First enantioselective synthesis of (−)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan

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First enantioselective synthesis of (−)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan

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