A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives

A concise synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was s...

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Autores principales: Wojtkielewicz, Agnieszka, Pawelski, Damian, Bazydło, Przemysław, Baj, Aneta, Witkowski, Stanisław, Morzycki, Jacek W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7287600/
https://www.ncbi.nlm.nih.gov/pubmed/32443910
http://dx.doi.org/10.3390/molecules25102377
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author Wojtkielewicz, Agnieszka
Pawelski, Damian
Bazydło, Przemysław
Baj, Aneta
Witkowski, Stanisław
Morzycki, Jacek W.
author_facet Wojtkielewicz, Agnieszka
Pawelski, Damian
Bazydło, Przemysław
Baj, Aneta
Witkowski, Stanisław
Morzycki, Jacek W.
author_sort Wojtkielewicz, Agnieszka
collection PubMed
description A concise synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was subjected to cyclization with Et(3)SiH/TFA or Et(3)SiH/Bi(TfO)(3). Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. N-Alkyl derivatives were also obtained in a similar way.
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spelling pubmed-72876002020-06-15 A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives Wojtkielewicz, Agnieszka Pawelski, Damian Bazydło, Przemysław Baj, Aneta Witkowski, Stanisław Morzycki, Jacek W. Molecules Article A concise synthesis of (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was subjected to cyclization with Et(3)SiH/TFA or Et(3)SiH/Bi(TfO)(3). Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. N-Alkyl derivatives were also obtained in a similar way. MDPI 2020-05-20 /pmc/articles/PMC7287600/ /pubmed/32443910 http://dx.doi.org/10.3390/molecules25102377 Text en © 2020 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
Pawelski, Damian
Bazydło, Przemysław
Baj, Aneta
Witkowski, Stanisław
Morzycki, Jacek W.
A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives
title A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives
title_full A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives
title_fullStr A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives
title_full_unstemmed A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives
title_short A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives
title_sort convenient synthesis of (16s,20s)-3β-hydroxy-5α-pregnane-20,16-carbolactam and its n-alkyl derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7287600/
https://www.ncbi.nlm.nih.gov/pubmed/32443910
http://dx.doi.org/10.3390/molecules25102377
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