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Synfacts 2009(2): 0125-0125  
DOI: 10.1055/s-0028-1087611
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Salinosporamide A

Contributor(s): Philip Kocienski, Zofia Komsta
K. Takahashi, M. Midori, K. Kawano, J. Ishihara, S. Hatakeyama*
Nagasaki University, Japan
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Publikationsverlauf

Publikationsdatum:
22. Januar 2009 (online)

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Significance

(-)-Salinosporamide A, isolated from the marine bacterium, inhibits proteasome 20S activity. Thus, it is of interest as a potent anticancer agent. The focal step of the synthesis is the construction of the pyrrolidinone core via a high-yielding indium(III)-catalyzed Conia-ene-type cyclization (C → D).