213411-13-3Relevant academic research and scientific papers
Stereoselective Total Synthesis of (±)-Swainsonine Based on Endo Mode Cyclization
Mukai, Chisato,Sugimoto, Yu-Ichi,Miyazawa, Kana,Yamaguchi, Sumie,Hanaoka, Miyoji
, p. 6281 - 6287 (1998)
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.
