Investigation into the Synthesis of C-25 Oxysterols

Abstract

A simple and environmentally benign method for the preparation of 25-hydroxycholesterol, a modulator of cholesterol biosynthesis, has been developed. The final product can be obtained by the reaction of mCPBA and 24-dehydrocholesterol, followed by reduction with lithium aluminium hydride in THF in moderate yields.

Advances in Steroid Chemistry

“…The synthesis of a novel vitamin D analogue, 24(28)-methylene-lα-hydroxyvitamin D 3 has been reported, whilst investigations into the synthesis of C-25 oxysterols have been described 5 in the context of modifications to the sterol side chain. 5α-Reductase inhibitors are targets in the development of drugs for the treatment of prostate cancer.…”

A Facile Synthesis of 3β,25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor

“…A chemical transformation to introduce a 25-hydroxy group into an appropriate substrate would be a key step in the preparation of 3β,25-dihydroxy-5α-cholest-7-ene 1. Zhao et al 11 reported a synthesis for the preparation of oxysterols from desmosterol. The key step in the introduction of the 25-hydroxy group was achieved via a ringopening reaction of epoxide prepared with chloroperoxybenzoic acid and by reduction with LiAlH 4 .…”