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Formal Total Synthesis of (+)-Zaragozic Acid C through an Ireland–Claisen Rearrangement

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  • Financial support for this study was provided by the Australian Research Council: Discovery-Grants Program and the Deutsche Forschungsgemeinschaft (DFG postdoctoral fellowship to J.O.B.).

Abstract

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A simple rearrangement: A formal total synthesis of zaragozic acid C (1) was achieved by the synthesis of intermediate 2. The key step involves an Ireland–Claisen rearrangement of an allylic ester to generate a carbon–carbon bond and two asymmetric centers simultaneously.

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