Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland.
Molecules. 2019 Mar 21;24(6):1132. doi: 10.3390/molecules24061132.
A two-step synthesis of solasodine pivalate from diosgenin pivalate is described. The key transformation involves the reaction of diosgenin pivalate with benzyl carbamate (CbzNH₂) promoted by TMSOTf. During the reaction the F-ring of the spiroketal moiety opens up with a simultaneous introduction of a Cbz-protected amino group in position 26. A one-pot deprotection of 26-amine with AcBr/BuOH followed by the -cyclization affords solasodine pivalate in 45% overall yield.
描述了从薯蓣皂素 pivalate 经两步合成 Solasodine pivalate。关键的转化涉及薯蓣皂素 pivalate 与苄基氨基甲酸酯（CbzNH₂）在 TMSOTf 促进下的反应。反应过程中，螺缩酮部分的 F 环打开，同时在 26 位引入 Cbz 保护的氨基。一锅法用 AcBr/BuOH 脱除 26-位的氨基，然后环化得到 Solasodine pivalate，总收率为 45%。
