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.
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%.
Yamauchi
Satoshi
S
Faculty of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan. syamauch@agr.ehime-u.ac.jp
Nakato
Tomofumi
T
Tsuchiya
Masahiro
M
Akiyama
Koichi
K
Maruyama
Masafumi
M
Sugahara
Takuya
T
Kishida
Taro
T
D001593:Benzyl Compounds / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism