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

Bischoff, Matthias; Sippel, Claudia; Bracher, Andreas; Hausch, Felix

doi:10.1021/ol5023195

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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

MPS-Authors

/persons/resource/persons77798

Bracher, Andreas
Hartl, Franz-Ulrich / Cellular Biochemistry, Max Planck Institute of Biochemistry, Max Planck Society;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

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-0000-0024-4564-0

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.