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dc.contributor.authorFairhurst, Magnus John E.
dc.contributor.authorMuhammad, Zeeshan
dc.contributor.authorHaug, Bengt Erik
dc.contributor.authorBayer, Annette
dc.date.accessioned2018-08-01T06:34:19Z
dc.date.available2018-08-01T06:34:19Z
dc.date.issued2018
dc.PublishedFairhurst MJE, Muhammad M, Haug BE, Bayer A. Aldol condensations on a 3-alkylidene-2,5-diketopiperazine - synthesis of two marine natural products. Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry. 2018;29(10):1303-1306eng
dc.identifier.issn1437-2096en_US
dc.identifier.issn0936-5214en_US
dc.identifier.urihttps://hdl.handle.net/1956/17929
dc.descriptionUnder embargo until: 01.01.2019
dc.description.abstractThe synthesis of two marine natural products containing a 3-alkylidene-6-arylidene-2,5-diketopiperazine scaffold by employing two consecutive aldol condensations starting with 1,4-diacetyl-2,5-diketopiperazine is reported. The target compounds contain a phenol or an imidazole group as aryl substituents, respectively, and suitable conditions for the aldol condensation of 1-acyl-3-alkylidene-2,5-diketopiperazine with the required functionalised aromatic aldehydes were developed. Provided the optimal base was used, introduction of the phenol group did not require use of a protecting group. Boc-protection was beneficial for introduction of the imidazole group, and conditions for carrying out the aldol condensation and Boc-deprotection in one step were identified. The stereochemistry of the target compounds was confirmed by NMR analysis.en_US
dc.language.isoengeng
dc.publisherThieme Publishingen_US
dc.subject2,5-diketopiperazineeng
dc.subjectnatural producteng
dc.subjecttotal synthesiseng
dc.subject­aldol condensationeng
dc.titleAldol condensations on a 3-alkylidene-2,5-diketopiperazine - synthesis of two marine natural productsen_US
dc.typePeer reviewed
dc.typeJournal article
dc.date.updated2018-03-20T09:00:13Z
dc.description.versionacceptedVersionen_US
dc.rights.holderCopyright 2018 Georg Thieme Verlagen_US
dc.identifier.doihttps://doi.org/10.1055/s-0036-1591755
dc.identifier.cristin1545604
dc.source.journalSynlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
dc.relation.projectNorges forskningsråd: 224790


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