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Synfacts 2007(2): 0130-0130  
DOI: 10.1055/s-2006-955769
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of (+)-Zaragozic Acid C

Contributor(s): Philip Kocienski, Thomas Snaddon
J. O. Bunte, A. N. Cuzzupe, A. M. Daly, M. A. Rizzacasa*
The University of Melbourne, Australia
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

The zaragozic acids (squalestatins) are fungal metabolites that display cholesterol-lowering activity and inhibition of farnesyl protein transferase. This approach to (+)-zaragozic acid C is noteworthy for the use of an Ireland-Claisen rearrangement to install two contiguous quaternary centers (C→E). For a related strategy, see the synthesis of (-)-cinnatrin B by Rizzacasa and co-workers: J. Org. Chem. 2002, 67, 4392-4398.