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https://hdl.handle.net/2440/134460
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DC Field | Value | Language |
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dc.contributor.author | Sassnink, S.A. | - |
dc.contributor.author | Phan, Q.D. | - |
dc.contributor.author | Lam, H.C. | - |
dc.contributor.author | Day, A.J. | - |
dc.contributor.author | Murray, L.A.M. | - |
dc.contributor.author | George, J.H. | - |
dc.date.issued | 2022 | - |
dc.identifier.citation | Organic and Biomolecular Chemistry, 2022; 20(8):1759-1768 | - |
dc.identifier.issn | 1477-0520 | - |
dc.identifier.issn | 1477-0539 | - |
dc.identifier.uri | https://hdl.handle.net/2440/134460 | - |
dc.description.abstract | Oxidative degradation and rearrangement of polycyclic polyprenylated acylphloroglucinols (PPAPs) has created diverse families of unique natural products that are attractive targets for biomimetic synthesis. Herein, we report a racemic synthesis of hyperibrin A and its oxidative radical cyclization to give yezo'otogirin C, followed by epoxidation and House-Meinwald rearrangement to give hypermogin D. We also investigated the biomimetic synthesis of norascyronone A via a similar radical cyclization pathway, with unexpected results that give insight into its biosynthesis. | - |
dc.description.statementofresponsibility | Stefania A. Sassnink, Quang D. Phan, Hiu C. Lam, Aaron J. Day, Lauren A.M. Murray and Jonathan H. George | - |
dc.language.iso | en | - |
dc.publisher | Royal Society of Chemistry | - |
dc.rights | This journal is © The Royal Society of Chemistry 2022 | - |
dc.source.uri | http://dx.doi.org/10.1039/d2ob00074a | - |
dc.subject | Terpenes | - |
dc.subject | Phloroglucinol | - |
dc.subject | Biological Products | - |
dc.subject | Molecular Structure | - |
dc.subject | Biomimetic Materials | - |
dc.title | Biomimetic synthesis of the non-canonical PPAP natural products yezo'otogirin C and hypermogin D, and studies towards the synthesis of norascyronone A | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1039/d2ob00074a | - |
dc.relation.grant | http://purl.org/au-research/grants/arc/DP200102964 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Murray, L.A.M. [0000-0003-3249-0828] | - |
dc.identifier.orcid | George, J.H. [0000-0002-7330-2160] | - |
Appears in Collections: | Chemistry publications |
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