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Open AccessArticle

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

Faculty of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, Poland
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Academic Editor: Rafal R. Sicinski
Molecules 2020, 25(10), 2377; https://doi.org/10.3390/molecules25102377
Received: 3 May 2020 / Revised: 18 May 2020 / Accepted: 19 May 2020 / Published: 20 May 2020
(This article belongs to the Special Issue Steroids-II)
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 Et3SiH/TFA or Et3SiH/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. View Full-Text
Keywords: lactams; reductive amination; spirostane degradation; steroids lactams; reductive amination; spirostane degradation; steroids
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Wojtkielewicz, A.; Pawelski, D.; Bazydło, P.; Baj, A.; Witkowski, S.; Morzycki, J.W. A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives. Molecules 2020, 25, 2377.

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