Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate

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(2)) promoted by TMSOTf. During the reaction the F-ring of the spiroketal moiety opens up with a simultaneous introduction...

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Autores principales: Wojtkielewicz, Agnieszka, Kiełczewska, Urszula, Morzycki, Jacek W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471385/
https://www.ncbi.nlm.nih.gov/pubmed/30901960
http://dx.doi.org/10.3390/molecules24061132
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author Wojtkielewicz, Agnieszka
Kiełczewska, Urszula
Morzycki, Jacek W.
author_facet Wojtkielewicz, Agnieszka
Kiełczewska, Urszula
Morzycki, Jacek W.
author_sort Wojtkielewicz, Agnieszka
collection PubMed
description 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(2)) 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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spelling pubmed-64713852019-04-26 Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate Wojtkielewicz, Agnieszka Kiełczewska, Urszula Morzycki, Jacek W. Molecules Article 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(2)) 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. MDPI 2019-03-21 /pmc/articles/PMC6471385/ /pubmed/30901960 http://dx.doi.org/10.3390/molecules24061132 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wojtkielewicz, Agnieszka
Kiełczewska, Urszula
Morzycki, Jacek W.
Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
title Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
title_full Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
title_fullStr Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
title_full_unstemmed Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
title_short Two-step Synthesis of Solasodine Pivalate from Diosgenin Pivalate
title_sort two-step synthesis of solasodine pivalate from diosgenin pivalate
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471385/
https://www.ncbi.nlm.nih.gov/pubmed/30901960
http://dx.doi.org/10.3390/molecules24061132
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