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Synfacts 2009(7): 0700-0700  
DOI: 10.1055/s-0029-1217252
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Zaragozic Acid C

Contributor(s): Philip Kocienski, Zofia Komsta
D. A. Nicewicz, A. D. Satterfield, D. C. Schmitt, J. S. Johnson*
University of North Carolina at Chapel Hill, USA
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

The zaragozic acids are picomolar inhibitors of squalene synthase, an enzyme that catalyzes the first step in cholesterol biosynthesis. They also enhance radiochemotheraphy of acute myeloid leukemia cell lines. This formal synthesis features the use of silyl glyoxylate A as a geminal dipolar glyoxylate synthon in the diastereoselective synthesis of C.