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https://hdl.handle.net/2440/139346
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dc.contributor.author | zur Bonsen, A.B. | - |
dc.contributor.author | Sumby, C.J. | - |
dc.contributor.author | George, J.H. | - |
dc.date.issued | 2023 | - |
dc.identifier.citation | Organic Letters, 2023; 25(34):6317-6321 | - |
dc.identifier.issn | 1523-7060 | - |
dc.identifier.issn | 1523-7052 | - |
dc.identifier.uri | https://hdl.handle.net/2440/139346 | - |
dc.description | Published: August 22, 2023 | - |
dc.description.abstract | Hyperireflexolides A and B were synthesized in six steps via the dearomatization and fragmentation of a simple acylphloroglucinol starting material. The dearomatized acylphloroglucinol undergoes a sequence of oxidative radical cyclization, retro-Dieckmann fragmentation, stereodivergent intramolecular carbonyl-ene reactions, and final α-hydroxy-β-diketone rearrangements to give the target natural products. This sequence is based on a biosynthetic proposal that claims the hyperireflexolides as highly rearranged polycyclic polyprenylated acylphloroglucinols (PPAPs), which is supported by the structural revision of hyperireflexolide B. | - |
dc.description.statementofresponsibility | Andreas B. zur Bonsen, Christopher J. Sumby, and Jonathan H. George | - |
dc.language.iso | en | - |
dc.publisher | American Chemical Society (ACS) | - |
dc.rights | © 2023 American Chemical Society | - |
dc.source.uri | http://dx.doi.org/10.1021/acs.orglett.3c02232 | - |
dc.subject | Chemical synthesis; Fragmentation; Organic synthesis; Pharmaceuticals; Rearrangement | - |
dc.title | Bioinspired Total Synthesis of Hyperireflexolides A and B | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/acs.orglett.3c02232 | - |
dc.relation.grant | http://purl.org/au-research/grants/arc/DP200102964 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | zur Bonsen, A.B. [0000-0001-9111-3876] | - |
dc.identifier.orcid | Sumby, C.J. [0000-0002-9713-9599] | - |
dc.identifier.orcid | George, J.H. [0000-0002-7330-2160] | - |
Appears in Collections: | Chemistry publications |
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