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

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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

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.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-4564-0 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-4565-E

Genre: Journal Article

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Creators:
Bischoff, Matthias¹, Author
Sippel, Claudia¹, Author
Bracher, Andreas², Author
Hausch, Felix¹, Author

Affiliations:
1external, ou_persistent22
2Hartl, Franz-Ulrich / Cellular Biochemistry, Max Planck Institute of Biochemistry, Max Planck Society, ou_1565152

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Free keywords: PEPTIDYL-PROLYL ISOMERASE; IMMUNOSUPPRESSANT FK506; ASYMMETRIC EPOXIDATION; DERIVATIVES; LIGANDS; FKBP52; INHIBITION; EFFICIENCY; RAPAMYCIN; KETONE

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.

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Language(s): eng - English

Dates: Date issued: 2014

Publication Status: Issued

Pages: 4

Publishing info: -

Table of Contents: -

Rev. Type: Peer

Identifiers: ISI: 000343526200006
DOI: 10.1021/ol5023195

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Title: ORGANIC LETTERS

Source Genre: Journal

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Publ. Info: 1155 16TH ST, NW, WASHINGTON, DC 20036 USA : AMER CHEMICAL SOC

Pages: - Volume / Issue: 16 (20) Sequence Number: - Start / End Page: 5254 - 5257 Identifier: ISSN: 1523-7060