Synthesis of the new mannosidase inhibitors, diversity-oriented 5-substituted swainsonine analogues, via stereoselective Mannich reaction.
5alpha-substituted swainsonine analogues were synthesized by Mannich reaction of an in situ generated (-)-swainsonine iminium ion intermediate. 5alpha-substituted swainsonine analogues were epimerized to their 5beta-isomers in protic solvent. [reaction: see text]
Fujita
Tomoya
T
Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima, Minamijosanjimacho-2, Tokushima 770-8506 Japan.
Nagasawa
Hideko
H
Uto
Yoshihiro
Y
Hashimoto
Toshihiro
T
Asakawa
Yoshinori
Y
Hori
Hitoshi
H
D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D008361:Mannosidases / Q000037:antagonists & inhibitors*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D017026:Swainsonine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D004791:Enzyme Inhibitors; D008361:Mannosidases; D017026:Swainsonine