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Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate.

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 (CbzNH?) 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.

SUBMITTER: Wojtkielewicz A

PROVIDER: S-EPMC6471385 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate.

Wojtkielewicz Agnieszka A Kiełczewska Urszula U Morzycki Jacek W JW

Molecules (Basel, Switzerland) 20190321 6

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 <i>N</i>-cyclization affords solasodine pivalate in 45% overall yield. ...[more]

PMID: 30901960

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