A concise synthesis of 25-hydroxycholesterol from hyodesoxycholic acid

作者：Jin, Can; Wang, Yulei; Sun, Bin; Su, Weike^*

来源：Journal of Chemical Research, 2018, 42(2): 96-99.

DOI：10.3184/174751918X15184426915885

• hyodesoxycholic acid
• di-isobutylaluminium hydride
• 3 beta-tetrahydropyranyloxychol-5-en-24-al
• hydroxybromination
• 25-hydroxycholesterol

A simple, efficient and economical method has been developed for the synthesis of 25-hydroxycholesterol in seven steps from hyodesoxycholic acid with an overall yield of 39%. The preparation of the 3 beta-tetrahydropyranyloxychol-5-en-24-al from 3 beta-tetrahydropyranyloxychol-5-en-24-oic acid methyl ester with di-isobutylaluminium hydride was achieved instead of using the conventional two-step reaction, thus avoiding the use of the toxic oxidant CrO3. The terminal product was obtained by hydroxybromination of desmosterol with N-bromosuccinimide/H2O, followed by reduction and deprotection of the halohydrins with LiAlH4. This simplified route gave an increased overall yield and used economical and environmentally benign reagents.

• 出版日期2018-2
• 单位浙江工业大学