苄基甲磺酸酯在四氢呋喃木脂素合成中的应用：7,8-反式、7',8'-反式、7,7'-顺式和8,8'-顺式virgatusin立体异构体的合成。

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.

作者信息

Yamauchi Satoshi, Nakato Tomofumi, Tsuchiya Masahiro, Akiyama Koichi, Maruyama Masafumi, Sugahara Takuya, Kishida Taro

机构信息

Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan.

出版信息

Biosci Biotechnol Biochem. 2007 Sep;71(9):2248-55. doi: 10.1271/bbb.70236. Epub 2007 Sep 7.

DOI:10.1271/bbb.70236

PMID:17827688

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%.

摘要

使用甲磺酸苄酯来构建四取代四氢呋喃木脂素，以避免傅克类型的反应。合成了光学纯的7,8-反式、7',8'-反式、7,7'-顺式和8,8'-顺式virgatusin立体异构体。对映体过量>>99%。