168131-47-3Relevant academic research and scientific papers
Synthesis of 3α,7α,12α-trihydroxy- and 3α,7α-dihydroxy-5β-cholestan-26-oic acids by the use of β-ketosulfoxide
Kurosawa, Takao,Nakano, Hiroyuki,Sato, Masahiro,Tohma, Masahiko
, p. 509 - 514 (2007/10/03)
The biosynthetic intermediates of bile acid, 3α,7α,12α-trihydroxy- and 3α,7α-dihydroxy-5β-cholestan-26-oic acids, were synthesized by means of the thermal elimination of β-ketosulfoxides.The α,β-unsaturated ketones as key compounds of the synthesis, 3α,7α,12α-trihydroxy- and 3α,7α-dihydroxy-5β-cholest-25-en-24-ones, were effectively derived from the β-ketosulfoxides prepared from methyl cholate or chenodeoxycholate by reaction with methylsulfinylcarbanion.These unsaturated ketones were converted into 3α,7α,12α,26-tetrahydroxy- and 3α,7α,26-trihydroxy-5β-cholestanes by reductive deoxygenation and hydroboration, of which stereoisomers were chromatographically separated into 25S- and 25R-isomers.The oxidation of each of the above isomeric alcohols after the protection of the hydroxyl groups on the steroidal ring and the following hydrolysis gave the title 26-carboxylic acids. - Keywords: C27-bile acid, bile alcohol, β-ketosulfoxide, thermal elimination, stereoisomer
