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Synfacts 2011(9): 0932-0932  
DOI: 10.1055/s-0030-1260912
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Trichostatin A

Contributor(s): Philip Kocienski
C. C. Cosner, P. Helquist*
University of Notre Dame, USA
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Publikationsdatum:
19. August 2011 (online)

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Significance

Histone deacetylase (HDAC) inhibitors are of interest for the treatment of a wide range of disorders including cancer, inflammatory diseases, malaria, and motor neuron diseases. (R)-(+)-Trichostatin A, a natural product isolated from Streptomyces hygroscopicus, is a potent HDAC inhibitor. In this paper, two syntheses of ­racemic trichostatin A are described that feature a palladium-catalyzed cross-coupling of a Zn ­enolate and a bromo alkene as the key step.