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Synfacts 2006(2): 0103-0103  
DOI: 10.1055/s-2005-923598
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Ningalin D

Contributor(s): Philip Kocienski, Thomas Snaddon
A. Hamasaki, J. M. Zimpleman, I. Hwang, D. L. Boger*
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

Boger and co-workers have employed an inverse electron demand azadiene ­Diels-Alder reaction to construct the highly substituted symmetrical pyrrole G that was converted into the ATP-citrate lyase inhibitor Ningalin D (9 steps, 19% overall). This method offers an alternative to the plethora of existing metal-mediated coupling reactions on preformed halo-substituted pyrroles. For a recent synthesis of the related natural product Dictyodendrin B, see: A. Fürstner, M. M. Domostoj, B. Scheiper J. Am. Chem. Soc. 2005, 127, 11620-11621.