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Synfacts 2006(5): 0425-0425  
DOI: 10.1055/s-2006-934402
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Zaragozic Acid C

Contributor(s): Philip Kocienski
S. Nakamura, H. Sato, Y. Hirata, N. Watanabe, S. Hashimoto*
Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

The Zaragozic acids are picomolar competitive inhibitors of squalene synthase with potential for lowering serum cholesterol. The highly congested bicyclic acetal has attracted much interest culminating in seven total syntheses of the Zaragozic acids as well as a plethora of methods. This, the eighth synthesis, is noteworthy for its construction of two adjacent quaternary centers by an aldol reaction of α-keto ester A and ketene thioacetal B, the first time such a feat has been attempted.