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Synfacts 2006(5): 0413-0413  
DOI: 10.1055/s-2006-934400
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Rugulosin

Contributor(s): Philip Kocienski
K. C. Nicolaou, Y. H. Lim, C. D. Papageorgiou, J. L. Piper
Scripps Institute, La Jolla, USA
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Publikationsdatum:
21. April 2006 (online)

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Significance

A very simple oxidation of anthradihydroquinone C with manganese dioxide set in train a cascade of cyclizations leading to the complex, polycyclic framework of (+)-Rugulosin - a huge return for a small investment. The entire synthesis represents the apotheosis of the Michael reaction. The target molecule has potential anti-HIV properties.