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Synfacts 2008(3): 0227-0227  
DOI: 10.1055/s-2008-1042661
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Frondosin A

Contributor(s): Philip Kocienski, Zofia Komsta
B. M. Trost*, Y. Hu, D. B. Horne
Stanford University, USA
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Publikationsverlauf

Publikationsdatum:
21. Februar 2008 (online)

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Significance

(+)-Frondosin A was isolated from the marine sponge Dysidea frondosa. The frondosins are interleukin-8 receptor antagonists -thus potent novel anti-inflammatory agents. They also exhibit some anti-HIV activity. Key points of the synthesis are: (1) the Charette asymmetric cyclo­propanation by which A was transformed to C, (2) the Ru-catalyzed [5+2] cycloaddition (E→F) and (3) the ring expansion (H→I).