A bioinspired, one-step total synthesis of peshawaraquinone

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dc.contributor.authorVieira de Castro, T.
dc.contributor.authorHuang, D.M.
dc.contributor.authorSumby, C.J.
dc.contributor.authorLawrence, A.L.
dc.contributor.authorGeorge, J.H.
dc.date.issued2023
dc.description.abstractA 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.
dc.description.statementofresponsibilityTomas Vieira de Castro, David M. Huang, Christopher J. Sumby, Andrew L. Lawrence and Jonathan H. George
dc.identifier.citationChemical Science, 2023; 14(4):950-954
dc.identifier.doi10.1039/d2sc05377b
dc.identifier.issn2041-6520
dc.identifier.issn2041-6539
dc.identifier.orcidHuang, D.M. [0000-0003-2048-4500]
dc.identifier.orcidSumby, C.J. [0000-0002-9713-9599]
dc.identifier.orcidGeorge, J.H. [0000-0002-7330-2160]
dc.identifier.urihttps://hdl.handle.net/2440/137371
dc.language.isoen
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.granthttp://purl.org/au-research/grants/arc/DP200102964
dc.relation.granthttp://purl.org/au-research/grants/arc/LE210100163
dc.rights© 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.
dc.source.urihttps://doi.org/10.1039/d2sc05377b
dc.titleA bioinspired, one-step total synthesis of peshawaraquinone
dc.typeJournal article
pubs.publication-statusPublished

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