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Updated: Apr 26, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Facile entry to an efficient and practical enantioselective synthesis of a polycyclic cholesteryl ester transfer
Zhengxu S Han1, Yibo Xu, Daniel R Fandrick
1Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc. , 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877, United States.
Abstract:
An efficient enantioselective synthesis of the chiral polycyclic cholesteryl ester transfer protein (CETP) inhibitor 1 has been developed. The synthesis was rendered practical for large scale via the development of a modified Hantzsch-type reaction to prepare the sterically hindered pyridine ring, enantioselective hydrogenation of hindered ketone 6 utilizing novel BIBOP-amino-pyridine derived Ru complex, efficient ICl promoted lactone formation, and a BF3 mediated hydrogenation process for diastereoselective lactol reduction. This efficient route was successfully scaled to produce multikilogram quantities of challenging CETP drug candidate 1.
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