Total Synthesis of Peshawaraquinone

22 July 2022, Version 1
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.


A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-alpha-lapachone, is reported. Enabled by reversible oxa-6pi-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 synthesis and in situ dimerization of dehydro-alpha-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.


biomimetic synthesis
total synthesis
cascade reactions
pericyclic reactions

Supplementary materials

Supporting Information
Experimental procedures and characterization data for all compounds, and coordination geometries for DFT optimized intermediates.


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.