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https://hdl.handle.net/2440/134092
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DC Field | Value | Language |
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dc.contributor.author | Yahiaoui, O. | - |
dc.contributor.author | Murray, L.A.M. | - |
dc.contributor.author | Zhao, F. | - |
dc.contributor.author | Moore, B.S. | - |
dc.contributor.author | Houk, K.N. | - |
dc.contributor.author | Liu, F. | - |
dc.contributor.author | George, J.H. | - |
dc.date.issued | 2022 | - |
dc.identifier.citation | Organic Letters, 2022; 24(2):490-495 | - |
dc.identifier.issn | 1523-7052 | - |
dc.identifier.issn | 1523-7052 | - |
dc.identifier.uri | https://hdl.handle.net/2440/134092 | - |
dc.description | Published: January 7, 2022 | - |
dc.description.abstract | Motivated by the biosynthesis of azamerone, we report the first example of a diazo-Hooker reaction, which involves the formation of a phthalazine ring system by the oxidative rearrangement of a diazoketone. Computational studies indicate that the diazo-Hooker reaction proceeds via an 8π-electrocyclization followed by ring contraction and aromatization. The biosynthetic origin of the diazoketone functional group was also chemically mimicked using a related natural product, naphterpin, as a model system. | - |
dc.description.statementofresponsibility | Oussama Yahiaoui, Lauren A. M. Murray, Fengyue Zhao, Bradley S. Moore, Kendall N. Houk, Fang Liu, and Jonathan H. George | - |
dc.language.iso | en | - |
dc.publisher | American Chemical Society | - |
dc.rights | © 2022 American Chemical Society | - |
dc.source.uri | http://dx.doi.org/10.1021/acs.orglett.1c03810 | - |
dc.subject | Oxidation reactions; Biosynthesis; Aromatic compounds; Rearrangement; Aldol reactions | - |
dc.title | A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/acs.orglett.1c03810 | - |
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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