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Recent developments in corticoid synthesis.

M Do-Trong, W Kreiser, E Strube

    Journal of Steroid Biochemistry
    |July 1, 1983
    PubMed
    Summary
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    This study details a new industrial method for synthesizing corticoids from desoxycholic acid. Key steps include oxygen transposition and side-chain degradation, yielding a crucial 20-ketone intermediate for cortisol production.

    Area of Science:

    • Biochemistry
    • Organic Chemistry
    • Medicinal Chemistry

    Background:

    • Industrial synthesis of corticoids is crucial for pharmaceutical manufacturing.
    • Desoxycholic acid serves as a potential starting material for corticoid production.
    • Efficient chemical transformations are needed to optimize corticoid synthesis.

    Purpose of the Study:

    • To develop an improved industrial manufacturing process for corticoids.
    • To achieve selective transposition of an oxygen function and side-chain degradation.
    • To establish a key intermediate for the synthesis of various corticoid drugs.

    Main Methods:

    • Protection of the 3 alpha-hydroxyl group.
    • Dehydration of the 12 alpha-alcohol and subsequent iodination to form a 12 alpha-iodo-11-ketone.

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  • Reductive dehalogenation, saponification, oxidative decarboxylation, and ozonolytic cleavage.

    • Main Results:

    • Selective transposition of the 12 alpha-oxygen function to the 11-position was achieved with high yield.
    • Side-chain degradation was successfully performed, leading to a delta 20-22-olefin intermediate.
    • Ozonolytic cleavage yielded the 20-ketone 19, a pivotal compound in corticoid drug synthesis.

    Conclusions:

    • The developed method provides an efficient route for corticoid synthesis from desoxycholic acid.
    • The 20-ketone intermediate is readily accessible and essential for producing drugs like cortisol.
    • This process offers significant improvements for the industrial manufacture of corticoids.