Stereoselective Total Synthesis of (+/-)-Swainsonine Based on Endo Mode Cyclization.
A new stereoselective total synthesis of (+/-)-swainsonine is described. Successive treatment of cis-3,4-epoxy-7-(p-toluenesulfonamido)-1-heptyne with dicobalt octacarbonyl, Lewis acid, and cerium(IV) ammonium nitrate effected stereoselective formation of the trans-2-ethynyl-3-hydroxypiperidine skeleton with retention of configuration at the propynyl center. The piperidine derivative thus prepared was converted into the title compound efficiently.
Mukai
Chisato
C
Faculty of Pharmaceutical Sciences, Kanazawa University Takara-machi, Kanazawa 920, Japan.
Sugimoto Yi
Yu-ichi
Miyazawa
Kana
K
Yamaguchi
Sumie
S
Hanaoka
Miyoji
M