Lipase-catalyzed domino kinetic resolution of alpha-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (-)-rosmarinecine.
The title domino reactions were developed to directly provide tetrahydrofuro[3,4-c]isoxazole derivatives (5 and 9) in > or =90% ee from racemic alpha-hydroxynitrones (2 and 6), which were used in the concise asymmetric total synthesis of (-)-rosmarinecine .
Akai
Shuji
S
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka 565-0871, Japan.
Tanimoto
Kouichi
K
Kanao
Yukiko
Y
Omura
Sohei
S
Kita
Yasuyuki
Y
D002384:Catalysis; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D008968:Molecular Conformation; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007097:Imines; D011763:Pyrrolizidine Alkaloids; C429133:rosmarinecine; D008049:Lipase