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A Re(V)-Catalyzed C−N Bond-Forming Route to Human Lipoxygenase Inhibitors

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Department of Chemistry and Biochemistry, University of California−Santa Cruz, Santa Cruz, California 956064, and Department of Chemistry, University of California−Berkeley, Berkeley, California 94720
Cite this: Org. Lett. 2005, 7, 12, 2501–2504
Publication Date (Web):May 12, 2005
https://doi.org/10.1021/ol050897a
Copyright © 2005 American Chemical Society
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    Abstract

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    A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air- and moisture-tolerant rhenium−oxo complex is described. The ability to couple functionalized components allows for convergent approaches to nitrogen-containing heterocyclic compounds such as the marine antibiotic pentabromopseudilin. These compounds were assayed against human lipoxygenase and found to be both potent and selective.

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     University of California, Santa Cruz.

    ‡

     University of California, Berkeley.

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