179862-74-9Relevant academic research and scientific papers
Total synthesis of (+)-conagenin
Hatakeyama, Susumi,Fukuyama, Hiroko,Mukugi, Yasuko,Irie, Hiroshi
, p. 4047 - 4050 (2007/10/03)
The first total synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved in highly stereo- and enantioselective manner. The carboxylic acid moiety was synthesized starting with asymmetric aldor reaction of propiophenone with acetaldehyde followed by in situ syn-selective NaBH4 reduction. The amin acid moiety was synthesized based upon Et2AlCl catalyzed cyclization of the epoxy trichloroacetimidate prepared from (S)-methylglycidol. Condensation of both moieties and alkaline hydrolysis led to (+)-conagenin.
