Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/102466
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dc.contributor.authorLam, H.en
dc.contributor.authorSpence, J.en
dc.contributor.authorGeorge, J.en
dc.date.issued2016en
dc.identifier.citationAngewandte Chemie - International Edition, 2016; 55(35):10368-10371en
dc.identifier.issn1433-7851en
dc.identifier.issn1521-3773en
dc.identifier.urihttp://hdl.handle.net/2440/102466-
dc.description.abstractHyperjapones A–E and hyperjaponols A–C are complex natural products of mixed aromatic polyketide and terpene biosynthetic origin that have recently been isolated from Hypericum japonicum. We have synthesized hyperjapones A–E using a biomimetic, oxidative hetero-Diels–Alder reaction to couple together dearomatized acylphloroglucinol and cyclic terpene natural products. Hyperjapone A is proposed to be the biosynthetic precursor of hyperjaponol C through a sequence of: 1) epoxidation; 2) acid-catalyzed epoxide ring-opening; and 3)a concerted, asynchronous alkene cyclization and 1,2-alkyl shift of a tertiary carbocation. Chemical mimicry of this proposed biosynthetic sequence allowed a concise total synthesis of hyperjaponolC to be completed in which six carbon–carbon bonds, six stereocenters, and three rings were constructed in just four steps.en
dc.description.statementofresponsibilityHiu C. Lam, Justin T. J. Spence and Jonathan H. Georgeen
dc.language.isoenen
dc.publisherWileyen
dc.rights© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheimen
dc.source.urihttp://onlinelibrary.wiley.com/doi/10.1002/anie.201606091/abstracten
dc.subjectHypericum; Terpenes; Molecular Conformation; Stereoisomerism; Biomimetic Materials; Polyketidesen
dc.titleBiomimetic total synthesis of hyperjapones A–E and hyperjaponols A and Cen
dc.typeJournal articleen
dc.identifier.rmid0030051344en
dc.identifier.doi10.1002/anie.201606091en
dc.relation.granthttp://purl.org/au-research/grants/arc/DP160103393en
dc.identifier.pubid260083-
pubs.library.collectionPhysics publicationsen
pubs.library.teamDS11en
pubs.verification-statusVerifieden
pubs.publication-statusPublisheden
Appears in Collections:Physics publications

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