SIDE CHAIN MODIFIED STEROLS AS PROBES INTO INSECT MOLTING HORMONE METABOLISM. II: SYNTHESIS OF MONOFLUOROCHOLESTEROLS

Article abstract of DOI:10.1016/0039-128X(83)90018-1

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 <26-14C>-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.