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Synfacts 2007(5): 0452-0452  
DOI: 10.1055/s-2007-968387
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Amphidinolide E

Contributor(s): Philip Kocienski, Fiona Black
P. Va, W. R. Roush*
The Scripps Research Institute, Florida, Jupiter, USA
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

The cis-tetrahydrofuran ring of amphidinolide A is synthesized using a highly diastereoselective [3+2] annulation reaction. Deft use of Fe(CO)3 as protecting group led to successful esterification of a hindered secondary alcohol. For an alternative synthesis of amphidinolide A, see: E. Lee and co-workers Angew. Chem. Int. Ed. 2006, 45, 8019-8021.