dc.contributor.author | Fairhurst, Magnus John E. | |
dc.contributor.author | Muhammad, Zeeshan | |
dc.contributor.author | Haug, Bengt Erik | |
dc.contributor.author | Bayer, Annette | |
dc.date.accessioned | 2018-08-01T06:34:19Z | |
dc.date.available | 2018-08-01T06:34:19Z | |
dc.date.issued | 2018 | |
dc.Published | Fairhurst 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):1303-1306 | eng |
dc.identifier.issn | 1437-2096 | en_US |
dc.identifier.issn | 0936-5214 | en_US |
dc.identifier.uri | https://hdl.handle.net/1956/17929 | |
dc.description.abstract | The 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.iso | eng | eng |
dc.publisher | Thieme Publishing | en_US |
dc.subject | 2,5-diketopiperazine | eng |
dc.subject | natural product | eng |
dc.subject | total synthesis | eng |
dc.subject | aldol condensation | eng |
dc.title | Aldol condensations on a 3-alkylidene-2,5-diketopiperazine - synthesis of two marine natural products | en_US |
dc.type | Peer reviewed | |
dc.type | Journal article | |
dc.date.updated | 2018-03-20T09:00:13Z | |
dc.description.version | acceptedVersion | en_US |
dc.rights.holder | Copyright 2018 Georg Thieme Verlag | en_US |
dc.identifier.doi | https://doi.org/10.1055/s-0036-1591755 | |
dc.identifier.cristin | 1545604 | |
dc.source.journal | Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry | |
dc.source.pagenumber | 1303-1306 | |
dc.relation.project | Norges forskningsråd: 224790 | |
dc.identifier.citation | Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry. 2018;29(10):1303-1306 | |
dc.source.volume | 29 | |
dc.source.issue | 10 | |