A bioinspired, one-step total synthesis of peshawaraquinone
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Date
2023
Authors
Vieira de Castro, T.
Huang, D.M.
Sumby, C.J.
Lawrence, A.L.
George, J.H.
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Chemical Science, 2023; 14(4):950-954
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Tomas Vieira de Castro, David M. Huang, Christopher J. Sumby, Andrew L. Lawrence and Jonathan H. George
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Abstract
A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-a-lapachone, is reported. Enabled by reversible oxa-6p-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-a-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.
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© 2023 The Author(s). Published by the Royal Society of Chemistry. Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.