Synthesis of 15α-Fluoro-24, 25-dihydrolanosterol as a Potential Inhibitor and/or Mechanistic Probe for Lanosterol 14α-Demethylase

Masuo MORISAK; Tomoko IGATA; Satomi YAMAMOTO

doi:10.1248/cpb.48.1474

Masuo MORISAK, Tomoko IGATA, Satomi YAMAMOTO

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Keywords: lanosterol, 14α-demethylase, fluorination, diethylaminosulfor trifluoride, cholesterol, lanost-9-en-3β-ol

JOURNAL FREE ACCESS

2000 Volume 48 Issue 10 Pages 1474-1479

DOI https://doi.org/10.1248/cpb.48.1474

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Abstract

As a potential inhibitor and/or mechanistic probe for lanosterol 14α-demethylase, 15α-fluoro-24, 25-dihydrolanosterol was prepared by fluorination of 15α-hydroxy-24, 25-dihydrolanost-7-en-3β-yl benzoate with diethyl-aminosulfur trifluoride, followed by hydrogen chloride-catalyzed isomerization of the Δ⁷ to Δ⁸ and reductive cleavage of the benzoate.

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