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Synfacts 2009(10): 1073-1073  
DOI: 10.1055/s-0029-1217859
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Dibromophakellin

Contributor(s): Philip Kocienski, Arndt W. Schmidt
T. Imaoaka, O. Iwamoto, K.-i. Noguchi, K. Nagasawa*
Tokyo University of Agriculture and Technology, Japan
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

The marine pyrrole-imidazole ­alkaloid (+)-dibromophakellin was isolated from Pseudoaxinyssa cantharella. The enantiomer is a natural product as well. Many analogous compounds have also been isolated, but neither (+)- nor (-)-phakellin. The key step in this synthesis is an Overman rearrangement to construct the C-10 aminal.