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Open AccessArticle

Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate

Institute of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland
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Molecules 2019, 24(6), 1132; https://doi.org/10.3390/molecules24061132
Received: 24 February 2019 / Revised: 18 March 2019 / Accepted: 19 March 2019 / Published: 21 March 2019
(This article belongs to the Special Issue Steroids-II)
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. View Full-Text
Keywords: solasodine; tomatidinol; diosgenin; ketal cleavage; spirostanes; steroids solasodine; tomatidinol; diosgenin; ketal cleavage; spirostanes; steroids
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MDPI and ACS Style

Wojtkielewicz, A.; Kiełczewska, U.; Morzycki, J.W. Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate. Molecules 2019, 24, 1132.

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