Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids

Joshua A. Homer, Irene De Silvestro, Eilidh J. Matheson, Jake T. Stuart, Andrew L. Lawrence*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

The development of the first enantioselective para-Claisen rearrangement has been achieved. Using a chiral aluminum Lewis acid, illicinole is rearranged to give (-)-illicinone A (er 87:13), which can then be converted into more complex Illicium-derived prenylated phenylpropanoids. The absolute configurations of the natural products (+)-cycloillicinone and (-)-illicarborene A have been determined, and our results cast doubt on the enantiopurity of the natural samples.

Original languageEnglish
Pages (from-to)3248–3252
JournalOrganic letters
Volume23
Issue number9
Early online date15 Apr 2021
DOIs
Publication statusPublished - 7 May 2021

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