title: Stereoselective Total Synthesis of (+/-)-Swainsonine Based on Endo Mode Cyclization.
abstract: 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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kanazawa University Takara-machi, Kanazawa 920, Japan.
authors.forename: Chisato
authors.initials: C
authors.lastname: Mukai
authors.forename: Yu-ichi
authors.lastname: Sugimoto Yi
authors.forename: Kana
authors.initials: K
authors.lastname: Miyazawa
authors.forename: Sumie
authors.initials: S
authors.lastname: Yamaguchi
authors.forename: Miyoji
authors.initials: M
authors.lastname: Hanaoka