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Synfacts 2008(5): 0448-0448  
DOI: 10.1055/s-2008-1072712
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Upial

Contributor(s): Philip Kocienski, Arndt W. Schmidt
K. Takahashi, M. Watanabe, T. Honda*
Hoshi University, Tokyo, Japan
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Publikationsdatum:
23. April 2008 (online)

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Significance

(+)-Upial is a nonisoprenoid sesquiterpene isolated from the sponge Dysidea fragilis. The rare bicyclo[3.3.1]nonane ring system was constructed using an intramolecular carbonyl­-ene reaction (D→E).