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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Stereoselective Total Synthesis of (+/-)-Swainsonine Based on Endo Mode Cyclization
Chisato Mukai1, Yu-ichi Sugimoto Yi, Kana Miyazawa
1Faculty of Pharmaceutical Sciences, Kanazawa University Takara-machi, Kanazawa 920, Japan.
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.
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