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Stereoselective Construction of the 5-Hydroxy Diazabicyclo[4.3.1]decane-2-one Scaffold, a Privileged Motif for FK506-Binding Proteins

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Bischoff,  Matthias
Dept. Translational Research in Psychiatry, Max Planck Institute of Psychiatry, Max Planck Society;

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Sippel,  Claudia
Dept. Translational Research in Psychiatry, Max Planck Institute of Psychiatry, Max Planck Society;

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Hausch,  Felix
Dept. Translational Research in Psychiatry, Max Planck Institute of Psychiatry, Max Planck Society;

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Citation

Bischoff, M., Sippel, C., Bracher, A., & Hausch, F. (2014). Stereoselective Construction of the 5-Hydroxy Diazabicyclo[4.3.1]decane-2-one Scaffold, a Privileged Motif for FK506-Binding Proteins. ORGANIC LETTERS, 16(20), 5254-5257. doi:10.1021/ol5023195.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-475E-0
Abstract
A stereoselective synthesis of a derivatized bicyclic [4.3.1]decane scaffold based on an acyclic precursor is described. The key steps involve a Pd-catalyzed sp(3)sp(2) Negishi-coupling, an asymmetric Shi epoxidation, and an intramolecular epoxide opening. Representative derivatives of this novel scaffold were synthesized and found to be potent inhibitors of the psychiatric risk factor FKBP51, which bound to FKBP51 with the intended molecular binding mode.