First enantioselective synthesis of (-)- and (+)-virgatusin, tetra-substituted tetrahydrofuran lignan.
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.
Yamauchi
Satoshi
S
Department of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan. syamauch@agr.ehime-u.ac.jp
Okazaki
Momotoshi
M
Akiyama
Koichi
K
Sugahara
Takuya
T
Kishida
Taro
T
Kashiwagi
Takehiro
T
D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
D005663:Furans; D017705:Lignans; C511226:virgatusin; C018674:tetrahydrofuran