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

ABSTRACT: A concise synthesis of (16S,20S)-3?-hydroxy-5?-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.

SUBMITTER: Wojtkielewicz A

PROVIDER: S-EPMC7287600 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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

Wojtkielewicz Agnieszka A Pawelski Damian D Bazydło Przemysław P Baj Aneta A Witkowski Stanisław S Morzycki Jacek W JW

Molecules (Basel, Switzerland) 20200520 10

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 ...[more]

PMID: 32443910

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