An efficient synthesis of (±)-narwedine and (±)-galanthamine by an improved phenolic oxidative coupling.
Old problems, new ideas! The biomimetic phenol coupling of norbelladine derivatives such as 1 (Bn = benzyl) to form galanthamine (2), a drug used in the treatment of Alzheimer's disease, has been greatly improved by the use of the hypervalent-iodine oxidation reagent phenyliodine(III) bis(trifluoroacetate) (PIFA).
Node
M
M
Department of Pharmaceutical Manufacturing Chemistry Kyoto Pharmaceutical University Misasagi, Yamashina, Kyoto 607-8414, Japan, Fax: (+81) 75-595-4775. node@mb.kyoto-phu.ac.jp.
Kodama
S
S
Hamashima
Y
Y
Baba
T
T
Hamamichi
N
N
Nishide
K
K
biomimetic synthesis; drug research; enzyme inhibitors; iodine reagents; oxidation