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  • Title: Side chain modified sterols as probes into insect molting hormone metabolism. II: synthesis of monofluorocholesterols.
    Author: Prestwich GD, Hong MS, Gayen AK.
    Journal: Steroids; 1983 Jan; 41(1):79-94. PubMed ID: 6658865.
    Abstract:
    The hydroxylations of the cholesterol side chain at C-20, 22, and 25 are key terminal events in ecdysone biogenesis. We have prepared the C-20, C-22, C-24, and C-25 monofluorinated cholesterols as potential inhibitors of these hydroxylation events, and preliminary bioassay results in Manduca sexta are reported. The synthesis of [26(14)C]-20-fluorocholesterol is also described. Although the 20-, 22-, and 25-monofluorocholesterols do not appear to affect larval growth and development, the 24-fluoro isomer shows a moderate retardation of growth and a modest increase in mortality.
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