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Synfacts 2007(8): 0794-0794  
DOI: 10.1055/s-2007-968717
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Paecilomycine A

Contributor(s): Philip Kocienski, Thomas Snaddon
S.-J. Min, S. J. Danishefsky*
Columbia University and Sloan-Kettering Institute for Cancer Research, New York, USA
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Paecilomycine A exhibits potent neurotrophic activity by elevation of nerve growth factor expression. Key to this synthesis is (1) an endo-selective Diels-Alder reaction to install a quaternary center, and (2) an intermolecular Pauson-Khand reaction to prepare a complex tricyclic cyclopentenone in a concise fashion.