First asymmetric total syntheses of fawcettimine-type Lycopodium alkaloids, lycoposerramine-C and phlegmariurine-A.
A successful asymmetric total synthesis of lycoposerramine-C involving such key steps as a cobalt-mediated Pauson-Khand reaction and vinyl Claisen rearrangement and its biomimetic transformation to phlegmariurine-A are described.
Nakayama
Atsushi
A
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Kogure
Noriyuki
N
Kitajima
Mariko
M
Takayama
Hiromitsu
H
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure
D000470:Alkaloids; C524731:fawcettimine; C546484:lycoposerramine-C; C546483:phlegmariurine-A