A Convenient Synthesis Of (16S,20S)-3β-Hydroxy-5α-Pregnane-20,16-Carbolactam And Its N-Alkyl Derivatives

    May 2020 in “ Molecules
    Agnieszka Wojtkielewicz, Damian Pawelski, Przemysław Bazydło, Aneta Baj, Stanisław Witkowski, Jacek W. Morzycki
    TLDR A new, efficient method was developed to synthesize a specific compound and its derivatives.
    The document described a concise synthesis method for (16S,20S)-3β-hydroxy-5α-pregnane-20,16-carbolactam starting from tigogenin. The most efficient route involved opening the lactone ring with an aminoalane reagent, followed by oxidation using PDC or Dess-Martin. The resulting oxo-amide was then cyclized using Et3SiH/TFA or Et3SiH/Bi(TfO)3. Alternatively, the lactone was converted to an oxo-acid and underwent microwave-assisted reductive amination. N-Alkyl derivatives were synthesized using a similar approach.
    Discuss this study in the Community →

    Research cited in this study

    3 / 3 results

    Related Community Posts Join

    6 / 15 results

    Similar Research

    5 / 415 results