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Synfacts 2006(4): 0300-0300  
DOI: 10.1055/s-2006-932038
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Ustiltoxin D

Contributor(s): Philip Kocienski, Fiona Black
P. Li, C. D. Evans, M. M. Joullié*
University of Pennsylvania, Philadelphia, USA
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

The salient feature of this synthesis of Ustiloxin D is the construction of the unusual tertiary alkyl-aryl ether linkage using a regioselective Cu(I)-catalyzed nucleophilic cleavage of the aziridine G. In previous syntheses of the Ustiltoxins, the Joullié group used an SNAr reaction to construct the tertiary alkyl-aryl ether motif (J. Am. Chem. Soc. 2002, 124, 520-521) whereas Wandless et al. deployed an asymmetric allylic alkylation for the same purpose (J. Org. Chem. 2004, 69, 8810-8820).