Total syntheses of (+)-fawcettimine and (+)-lycoposerramine-B.
The total synthesis of (+)-fawcettimine was completed in a highly stereoselective manner starting from the oxatricyclo[7.3.0.0(1,5)]dodecanedione derivative. The crucial step in this total synthesis involves the efficient construction of the azonane framework by the intramolecular Mitsunobu reaction. Furthermore, the first total synthesis of (+)-lycoposerramine-B was also accomplished via the common synthetic intermediate.
Otsuka
Yasunari
Y
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Inagaki
Fuyuhiko
F
Mukai
Chisato
C
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D010091:Oximes; C524731:fawcettimine; C497861:lycoposerramine-B