Issue 4, 2023

A bioinspired, one-step total synthesis of peshawaraquinone


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.

Graphical abstract: A bioinspired, one-step total synthesis of peshawaraquinone

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Article information

Article type
Edge Article
27 Sep 2022
20 Dec 2022
First published
21 Dec 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 950-954

A bioinspired, one-step total synthesis of peshawaraquinone

T. Vieira de Castro, D. M. Huang, C. J. Sumby, A. L. Lawrence and J. H. George, Chem. Sci., 2023, 14, 950 DOI: 10.1039/D2SC05377B

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