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- Title
Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate.
- Authors
Wojtkielewicz, Agnieszka; Kiełczewska, Urszula; Morzycki, Jacek W.
- 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.
- Subjects
SOLASODINE; DIOSGENIN; KETALS; STEROIDS; BENZYL compounds; CARBAMATES
- Publication
Molecules, 2019, Vol 24, Issue 6, p1132
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules24061132