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

A concise synthesis of (16 ,20 )-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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-05, Vol.25 (10), p.2377
Main Authors: Wojtkielewicz, Agnieszka, Pawelski, Damian, Bazydło, Przemysław, Baj, Aneta, Witkowski, Stanisław, Morzycki, Jacek W
Format: Article
Language:English
Subjects:
Amination
Aqueous solutions
Cyclization
Hydrogenation
lactams
Lactones - chemical synthesis
Lactones - chemistry
Oxidation
Oxidation-Reduction
Pregnanes - chemical synthesis
Pregnanes - chemistry
Reagents
reductive amination
Ring opening
spirostane degradation
steroids
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Summary:A concise synthesis of (16 ,20 )-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 SiH/TFA or Et SiH/Bi(TfO) . Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. -Alkyl derivatives were also obtained in a similar way.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25102377