Stereocontrolled Synthesis of All Eight Stereoisomers of the Putative Anti-Androgen Cyoctol

    October 2004 in “ Tetrahedron
    Johann Mulzer, Ulrich Kaselow, Klaus-Dieter Graske, H. Kühne, Andreas Sieg, Harry J. Martin
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    TLDR Scientists made all eight versions of a compound called cyoctol, but found it's not an anti-androgen and it fully breaks down in the skin.
    In 2004, researchers successfully synthesized all eight stereoisomers of the putative anti-androgen cyoctol, a compound previously thought to have potential applications in treating alopecia and male pattern baldness. However, biological tests indicated that cyoctol is not an anti-androgen, contradicting previous literature. The study also found that cyoctol was completely metabolized when passing through the skin, potentially eliminating adverse systemic effects after dermal application. The synthesis process involved multiple steps and the use of various chemical reactions. The synthesized compounds were analyzed using NMR spectroscopy, IR spectroscopy, and mass spectrometry. Despite the findings, the researchers concluded that further biological tests were needed due to discrepancies between their results and the patent literature.
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