Synthesis of (24S)-Hydroxy- and (24S)-24,25-Epoxycholesterol Analogues, Potential Agonists of Nuclear LXR Receptors

V. A. Khripach#, V. N. Zhabinskii, A. V. Antonchick, and A. P. Antonchick

#Phone: +375 172 648 647; e-mail:
Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Kuprevicha 5/2, Minsk, 220141, Belarus
Received: March 29, 2006;  in final form: April 17, 2006

Abstract: A new approach to the synthesis of a series of isomeric 24-hydroxy-and 24,25-epoxysteroids starting from lithocholic acid was proposed. Sharpless asymmetric hydroxylation of intermediate Δ24-olefines was used as a reaction determining the stereochemistry of target compounds. The resulting derivatives are potential agonists of nuclear receptors LXRα and LXRβ and are potentially useful in the structure-function studies.

Key words: asymmetric hydroxylation, cholesterol, oxysterols, steroids

Russian Journal of Bioorganic Chemistry 2006, 32 (6): 586-594