85198-69-2Relevant academic research and scientific papers
Stereoselective Introduction of Steroid Side Chains. Synthesis of Chenodeoxycholic Acid
Wovkulich, Peter M.,Batcho, Andrew D.,Uskokovic, Milan R.
, p. 612 - 615 (1984)
A new short route to chenodeoxycholic acid has been developed.The synthesis is based on the stereoselective introduction of the steroidal side chain via an ene reaction of methyl acrylate and a (17Z)-ethylidene steroid prepared from androstenedione.
Potential bile acid metabolites. 25. Synthesis and chemical properties of stereoisomeric 3alpha,7alpha,16- and 3alpha,7alpha,15-trihydroxy-5beta-cholan-24-oic acids.
Iida, Takashi,Hikosaka, Masahiro,Kakiyama, Genta,Shiraishi, Keisuke,Schteingart, Claudio D,Hagey, Lee R,Ton-Nu, Huong-Thu,Hofmann, Alan F,Mano, Nariyasu,Goto, Junichi,Nambara, Toshio
, p. 1327 - 1334 (2002)
Epimeric 3alpha,7alpha,16- and 3alpha,7alpha,15-trihydroxy-5beta-cholan-24-oic acids and some related compounds were synthesized from chenodeoxycholic acid (CDCA) and ursodeoxycholic acid (UDCA), respectively. The key reaction involved one-step remote oxyfunctionalization of unactivated methine carbons at C-17 of CDCA and at C-14 of UDCA as their methyl ester-peracetate derivatives with dimethyldioxirane (DMDO). After dehydration of the resulting 17alpha- and 14alpha-hydroxy derivatives with POCl(3) or conc. H(2)SO(4), the respective Delta(16)- and Delta(14)-unsaturated products were subjected to hydration via hydroboration followed by oxidation to yield the 3,7,16- and 3,7,15-triketones, respectively. Stereoselective reduction of the respective triketones with tert-butylamine-borane complex afforded the epimeric 3alpha,7alpha,16- or 3alpha,7alpha,15-trihydroxy derivatives exclusively. A facile formation of the corresponding epsilon-lactones between the side chain carboxyl group at C-24 and the 16alpha- (or 16beta-) hydroxyl group in bile acids is also clarified.
Process and intermediates for the synthesis of Vitamin D3 metabolites and chenodeoxycholic acid
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, (2008/06/13)
The present disclosure is directed to a process for the synthesis of chenodeoxychloic acid, 25-hydroxycholesterol and 1α,25-dihydroxycholesterol from 17-keto steroids. A cholic acid side chain is stereospecifically introduced by reaction of the appropriate 17-keto steroid with ethyltriphenylphosphonium halides to produce the 17-ethylidene derivative which is allowed to react with acrylic acid esters or propiolic acid esters followed by hydrogenation.
