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Synfacts 2009(1): 0009-0009  
DOI: 10.1055/s-0028-1087232
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Halenaquinone

Contributor(s): Philip Kocienski, Arndt W. Schmidt
M. A. Kienzler, S. Suseno, D. Trauner*
University of California at Berkeley, USA
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Publication History

Publication Date:
18 December 2008 (online)

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Significance

A short access to enantiopure halenaquinone is reported, yielding the non-natural isomer (ent-C is as easily accessible). The key step of the synthesis is an inverse-electron-demand intramolecular Diels-Alder cycloaddition (IMDA) using a vinylquinone as the dienophile.