Organic Chemistry

Total Synthesis of Peshawaraquinone

Authors

Abstract

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.

Content

Thumbnail image of peshawaraquinone manuscript.pdf

Supplementary material

Thumbnail image of peshawaraquinone SI.pdf
Supporting Information
Experimental procedures and characterization data for all compounds, and coordination geometries for DFT optimized intermediates.