Synthesis of Ustiltoxin D

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 S_NAr 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).