Abstract
(22E)-3α,6α,7α,12α-Tetrahydroxy-5β-chol-22-en- 24-oic acid and its N-acylamidated conjugates with glycine or taurine were synthesized from cholic acid. The key reactions employed are: 1) degradation of the side chain in intermediary C24 3β,6β,7β,12β- tetrahydroxylated bile acid to the corresponding C22 23,24-dinor-aldehyde, followed by Wittig reaction with methyl (triphenylphosphoranylidene)acetate and 2) N-acylamidation of the unconjugated tetrahydroxy-Δ22-5β-cholenoic acid with glycine (or taurine) in the presence of diethylphosphorocyanide and triethylamine as coupling reagents.
Original language | English |
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Pages (from-to) | 1103-1106 |
Number of pages | 4 |
Journal | Chemical and Pharmaceutical Bulletin |
Volume | 58 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2010 Aug |
Keywords
- Bile acid
- Gycine conjugate
- N-acylamidation
- Taurine conjugate
- Tetrahydroxy-Δ-5β-cholenoic acid
- Wittig reaction
ASJC Scopus subject areas
- Chemistry(all)
- Drug Discovery