Abstract
Novel 21-trifluoropregnenolone ( 6), 21-trifluoroprogesterone ( 7) and related compounds 4a and 8 have been synthesized in high yields from 3β-acetoxyandrost-5-ene-17β-carbaldehyde ( 3). The key reaction was the conversion of 3 into the 21-trifluoromethyl-20-alcohol as a diastereomeric mixture ( 4) by trifluoromethyltrimethylsilane (TMS-CF 3) in the presence of tetrabutylammonium fluoride (TBAF). All compounds, including 6 and 7, were unambiguously characterized by IR, 1H and 19F NMR, high-resolution mass spectrometry (HRMS), and elemental analysis. On this basis, we concluded that the only report of an earlier synthesis of 6 and 7 13 is erroneous. Enzyme inhibition studies showed that 20 ξ-hydroxy-21-trifluoropregn-4-en-3-one ( 8) is a potent inhibitor (IC 50 value = 0.6 μM) of rat 17α-hydroxylase/17,20-lyase.
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