Download PDF
Synfacts 2011(11): 1159-1159  
DOI: 10.1055/s-0031-1289253
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Cholesterol Transporter NPC1L1 Inhibitor

Contributor(s): Philip Kocienski
Y. Jiang, X. Chen, Y. Zheng, Z. Xue, C. Shu, W. Yuan, X. Zhang*
Chengdu Institute of Organic Chemistry and Graduate School of Chinese Academy of Sciences, Beijing, P. R. of China
Further Information

Publication History

Publication Date:
19 October 2011 (online)

    Permissions and Reprints

Significance

The target molecule, an inhibitor of the cholesterol transporter NPC1L1, was a ­potential hypocholesterolemic agent (S. Larson, J. Pfefferkorn, C. Van Huis WO 2008/104875, 2008). The key step in the synthesis depicted is an organocatalytic asymmetric hydrosilylation of the α-acetoxy β-enamino ester A. A mechanism of the reaction has not been proposed at this stage. A further 14 examples of the asymmetric hydrosilylation are reported with yields being typically >90% and ee values >90% in 10 of 14 cases.