Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 12, Pages 5357-5363Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300746x
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Funding
- Danish National Research Foundation
- Danish Natural Science Research Council
- Carlsberg Foundation
- Lundbeck Foundation
- iNANO
- Aarhus University
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We have synthesized two isotopically labeled variants of the beta-amyloid binding compound FSB possessing C-13-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The C-13-isotope labeling was achieved applying a Pd-catalyzed methoxycarbonylation of the corresponding aryl chlorides with externally (ex situ) generated C-13-labeled CO. Application of the Shirakawa-Hayashi protocol for the Pd-catalyzed reduction of a dialkyne intermediate using D2O allowed for the selective deuterium labeling of the two trans-C,C double bonds of FSB.
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