The class
A domino Mukaiyama-Michael/Michael/Aldol cyclization efficiently builds pentasubstituted arene cores for potent CETP inhibitors (Angew Chem Int Ed Engl 1999)
Original title: Stereoselective Mukaiyama-Michael/Michael/Aldol Domino Cyclization as the Key Step in the Synthesis of Pentasubstituted Arenes: An Efficient Access to Highly Active Inhibitors of Cholesteryl Ester Transfer Protein (CETP)
Chemists describe a one-step domino Mukaiyama-Michael/Michael/Aldol cyclization that constructs a stereopentad intermediate, which is then aromatized to yield fivefold substituted, pharmacologically active arenes. This synthetic route provides efficient access to highly active CETP inhibitors, demonstrating that a strategy built around transient stereochemical control followed by prompt aromatization can be an efficient way to assemble the densely substituted arene cores found in this inhibitor class.
Original abstract
Seemingly heartbreaking for a stereochemist, the one-step selective construction of a stereopentad and its prompt destruction by aromatization has been proven to be an efficient strategy for the synthesis of fivefold substituted, pharmacologically highly active arenes (see scheme).
Summary written by cetpinhibition.org from the published abstract; figures as published. Page updated 19 August 2026. Methods.