Universität zu Köln

Krapf, Philipp ORCID: 0000-0003-1671-2443, Richarz, Raphael, Urusova, Elizaveta A., Neumaier, Bernd ORCID: 0000-0001-5425-3116 and Zlatopolskiy, Boris D. (2016). Seyferth-Gilbert Homologation as a Route to F-18-Labeled Building Blocks: Preparation of Radiofluorinated Phenylacetylenes and Their Application in PET Chemistry. Eur. J. Org. Chem., 2016 (3). S. 430 - 434. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

A convenient method for the preparation of hitherto unknown ([F-18]fluorophenyl)acetylenes ([F-18]FPAs) using the Seyferth-Gilbert homologation is reported. The novel building blocks were efficiently prepared from easily accessible [F-18]fluorobenzaldehydes by using the Bestmann-Ohira reagent. High radiochemical yields and excellent radiochemical purities were achieved within only 20 min of reaction time; 2- and 4-[F-18]FPAs were applied to prepare radiofluorinated heterocycles by using different cycloaddition and cross-coupling reactions. Additionally, these building blocks were used to prepare three novel PET tracers. Thus, an artificial radiofluorinated protected amino acid [F-18]10, a COX-2-specific ligand [F-18]14, and a PSMA-selective inhibitor [F-18]16 were obtained in high radiochemical yields.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Krapf, Philipp UNSPECIFIED orcid.org/0000-0003-1671-2443 UNSPECIFIED Richarz, Raphael UNSPECIFIED UNSPECIFIED UNSPECIFIED Urusova, Elizaveta A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Neumaier, Bernd UNSPECIFIED orcid.org/0000-0001-5425-3116 UNSPECIFIED Zlatopolskiy, Boris D. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-291657
DOI:	10.1002/ejoc.201501377
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2016
Number:	3
Page Range:	S. 430 - 434
Date:	2016
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language BETA-LACTAMS; BIOLOGICAL EVALUATION; COUPLING REACTION; MEMBRANE ANTIGEN; LATE-STAGE; CLICK; CYCLOADDITION; DESIGN; FLUORINATION; INHIBITORS Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/29165