Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
Agnieszka Wojtkielewicz, Urszula Kiełczewska, Jacek W. Morzycki
Molecules · 2019
doi:10.3390/molecules24061132 (opens in a new tab)
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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.
Abstract licence: CC BY
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