A bioinspired, one-step total synthesis of peshawaraquinone

Tomás Vieira de Castro, David M. Huang, Christopher J. Sumby, Andrew L. Lawrence, Jonathan H. George*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-α-lapachone, is reported. Enabled by reversible oxa-6π-electrocyclizations of 2H-pyran intermediates, the base-catalyzed dimerization sets up an intramolecular (3 + 2) cycloaddition, with the formation of six stereocenters during the cascade. Combining the generation and in situ dimerization of dehydro-α-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.

Original languageEnglish
JournalChemical Science
Early online date21 Dec 2022
Publication statusE-pub ahead of print - 21 Dec 2022


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