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Synfacts 2009(3): 0233-0233  
DOI: 10.1055/s-0028-1087689
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Exiguamine A

Contributor(s): Philip Kocienski, Indu Dager
M. Volgraf, J.-P. Lumb, H. C. Brastianos, G. Carr, M. K. W. Chung, M. Münzel, A. G. Mauk, R. J. Andersen*, D. Trauner*
University of California, Berkeley, USA; University of British Columbia, Vancouver, Canada; Ludwig-Maximilians-Universität München, Germany
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Publikationsdatum:
19. Februar 2009 (online)

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Significance

Exiguamine A is isolated from the marine sponge Neopetrosia exigua and is a potent inhibitor of indoleamine-2,3-dioxygenase, which in turn metabolizes tryptophan. This biomimetic synthesis relies on a cascade sequence involving intramolecular nucleophilic attack of a tertiary amine onto an o-quinone and tautomerization ­followed by an oxa-6π-electrocyclization (I → exiguamine A).