4802-74-8Relevant academic research and scientific papers
Synthesis of the antiproliferative agent hippuristanol and its analogues via Suárez cyclizations and Hg(II)-catalyzed spiroketalizations
Ravindar, Kontham,Reddy, Maddi Sridhar,Lindqvist, Lisa,Pelletier, Jerry,Deslongchamps, Pierre
experimental part, p. 1269 - 1284 (2011/04/26)
A full account of the synthesis of hippuristanol and its analogues is described. Hecogenin acetate was identified as a suitable and economical starting material for this work, and substrate-controlled stereoselection was obtained throughout the construction of the key spiroketal unit. Suárez cyclization was first used, but Hg(II)-catalyzed spiroketalization of the 3-alkyne-1,7-diol motif was finally identified as the most convenient strategy.(Figure Presented)
Efficient synthetic approach to potent antiproliferative agent hippuristanol via Hg(II)-catalyzed spiroketalization
Ravindar, Kontham,Reddy, Maddi Sridhar,Lindqvist, Lisa,Pelletier, Jerry,Deslongchamps, Pierre
supporting information; experimental part, p. 4420 - 4423 (2010/12/18)
Figure Presented. The steroidal natural product hippuristanol targets eukaryotic translation initiation factor (eIF)4A which plays a pivotal role in translation in eukaryotic cells. Now an efficient synthesis of hippuristanol from 11-ketotigogenin is reported. The synthesis features a rapid construction of a spiroketal unit via Hg(OTf)2-catalyzed oxidation/ spiroketalization of the 3-alkyn-1,7-diol motif.
The 14C radiolabelled synthesis of the cholesterol absorption inhibitor CP-148,623. A novel method for the incorporation of a 14C label in enones
DeNinno, Michael P.,McCarthy, Keith E.
, p. 11007 - 11020 (2007/10/03)
Isotopically labelled compounds play important roles in pharmaceutical research. New strategies for the synthesis of these compounds, carbon isotopes in particular, are needed due to the limited availability of labelled reagents. We have developed a novel method for the 14C labelling of enones and have applied it to the synthesis of a 14C radiolabelled version of the cholesterol absorption inhibitor CP-148,623. The key steps involve the 1,2 addition of [14C]methyl Grignard to a cyclic enone followed by the 'anomalous' ozonolysis of the resulting allylic alcohol utilizing a non-traditional basic work-up. In this two step procedure, the original enone was regenerated with a 14C carbon atom at the alpha position. After several standard chemical steps, the synthesis of [14C]CP-148,623 was completed. The method has also been applied to a series of other enones demonstrating the generality of the procedure for the introduction of carbon isotopes in enone systems.
