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Synfacts 2008(10): 1014-1014  
DOI: 10.1055/s-2008-1078282
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Brefeldin A

Contributor(s): Philip Kocienski, Zofia Komsta
Y. Wu*, J. Gao
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

(+)-Brefeldin A, a metabolite of the fungus Eupenicillium brefeldianum, is an inhibitor of intracellular protein transport. It specifically and reversibly blocks protein transport to the Golgi apparatus, thus becoming an important tool for cell biologists. The synthesis features an intramolecular cyclization to form the five-membered ring core (C → D) and a Rh-catalyzed Michael addition (E + F → G).