Visible-light photoredox catalysis enables the biomimetic synthesis of nyingchinoids A, B, and D, and rasumatranin D

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dc.contributor.authorHart, J.D.
dc.contributor.authorBurchill, L.
dc.contributor.authorDay, A.J.
dc.contributor.authorNewton, C.G.
dc.contributor.authorSumby, C.J.
dc.contributor.authorHuang, D.M.
dc.contributor.authorGeorge, J.H.
dc.date.issued2019
dc.descriptionGerman edition
dc.description.abstractThe total synthesis of nyingchinoids A and B has been achieved through successive rearrangements of a 1,2-dioxane intermediate that was assembled using a visible-light photoredox-catalysed aerobic [2+2+2] cycloaddition. Nyingchinoid D was synthesised with a competing [2+2] cycloaddition. Based on NMR data and biosynthetic speculation, we proposed a structure revision of the related natural product rasumatranin D, which was confirmed through total synthesis. Under photoredox conditions, we observed the conversion of a cyclobutane into a 1,2-dioxane through retro-[2+2] cycloaddition followed by aerobic [2+2+2] cycloaddition.
dc.description.statementofresponsibilityJacob D. Hart, Laura Burchill, Aaron J. Day, Christopher G. Newton, Christopher J. Sumby, David M. Huang, and Jonathan H. George
dc.identifier.citationAngewandte Chemie International Edition, 2019; 131(9):2817-2820
dc.identifier.doi10.1002/ange.201814089
dc.identifier.issn0044-8249
dc.identifier.issn1521-3757
dc.identifier.orcidHart, J.D. [0000-0002-5318-518X]
dc.identifier.orcidNewton, C.G. [0000-0002-8962-5917]
dc.identifier.orcidSumby, C.J. [0000-0002-9713-9599]
dc.identifier.orcidHuang, D.M. [0000-0003-2048-4500]
dc.identifier.orcidGeorge, J.H. [0000-0002-7330-2160]
dc.identifier.urihttp://hdl.handle.net/2440/130744
dc.language.isoen
dc.publisherWiley
dc.relation.granthttp://purl.org/au-research/grants/arc/FT170100437
dc.rights© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.source.urihttps://doi.org/10.1002/ange.201814089
dc.subjectBiomimetic synthesis; cascade reactions; natural products; photoredox catalysis; total synthesis
dc.titleVisible-light photoredox catalysis enables the biomimetic synthesis of nyingchinoids A, B, and D, and rasumatranin D
dc.typeJournal article
pubs.publication-statusPublished

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