A Facile Synthesis of 3β, 25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor. (March 2018)

• Record Type: Journal Article
• Authors: Jin, Can; Liao, Zhibing; Sun, Bin; Xu, Tengwei
• Is Part Of: Journal of chemical research. Volume 42:Number 3(2018)
• Page Start: 156
• Page End: 159
• Publication Date: 2018-03
• Subjects: 3β, 25-dihydroxy-5α-cholest-7-ene -- 5α-cholesta-7, 24-diene-3β-toluene-sulfonate -- hydroxybromination -- 3-hydroxy-3-methylglutaryl coenzyme A reductase; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751918X15220628915420
• Languages: English
• ISSNs: 1747-5198

Abstract

An efficient four-step procedure is described for the synthesis of 3β, 25-dihydroxy-5α-cholest-7-ene from 3β-hydroxy-5α-cholesta-7, 24-diene in an overall yield of 34%. This product can serve as a precursor for the synthesis of an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. The 3β-toluene- p -sulfonate ester of 5α-cholesta-7, 24-diene was obtained from natural lanolin followed by treatment with toluene- p -sulfonyl chloride. The key step in the synthesis is a very mild method for the hydroxybromination of this ester with N -bromosuccinimide in water, followed by reduction with LiAlH4 to obtain the 3β-toluene- p -sulfonate ester of 25-hydroxy-5α-cholesta-7-ene. The final product was obtained after desulfonation of 3β-toluene- p -sulfonyoxy-25-hydroxy-5α-cholesta-7-ene to afford 3β, 25-dihydroxy-5α-cholest-7-ene in excellent yield. The reagents are all relatively cheap, non-toxic and stable.