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Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
Agnieszka Wojtkielewicz1, Urszula Kiełczewska2, Jacek W Morzycki3
1Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland. a.wojtkielewicz@uwb.edu.pl.
Abstract:
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 N-cyclization affords solasodine pivalate in 45% overall yield.
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