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- Title
A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives.
- Authors
Wojtkielewicz, Agnieszka; Pawelski, Damian; Bazydło, Przemysław; Baj, Aneta; Witkowski, Stanisław; Morzycki, Jacek W.; Sicinski, Rafal R.
- Abstract
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.
- Subjects
AMINATION; OXIDATION; LACTAMS
- Publication
Molecules, 2020, Vol 25, Issue 10, p2377
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules25102377