dc.contributor.author | Cirillo, Davide | |
dc.contributor.author | Karlsson, Staffan | |
dc.contributor.author | Bjørsvik, Hans-René | |
dc.date.accessioned | 2022-04-05T08:48:43Z | |
dc.date.available | 2022-04-05T08:48:43Z | |
dc.date.created | 2022-01-17T13:43:20Z | |
dc.date.issued | 2021 | |
dc.identifier.issn | 1434-193X | |
dc.identifier.uri | https://hdl.handle.net/11250/2989838 | |
dc.description.abstract | A selective oxidative Heck cross-coupling method was developed and optimized as a pivotal step for a synthetic route leading to the trans-stilbene framework. The developed method and synthesis were needed in a SAR study in progress that concerned design and development of an inhibitor for the human cell xCT antiporter system. The developed oxidative Heck cross-coupling method was examined with a variety of substrates and reagents to produce a library of different substituted trans-stilbenes, which revealed the method to hold a very good tolerance for an assortment of functional groups. The final synthetic route was successfully scaled-up (from mg scale) and performed in a 150 g (>1000×up-scaled) batch run to obtain an overall yield of 73 % (over three steps), which corresponds to a mean step yield of 90 %. The inhibitor candidate DC10 [(E)-5-(2-([1,1′-biphenyl]-4-yl)vinyl)-2-hydroxy-benzoic acid] was produced in multi-gram quantities (≈33 g) that subsequently was forwarded for animal efficacy and toxicology studies. The scaled-up process constitutes the first example of an oxidative Heck cross-coupling on >100-gram scale. | en_US |
dc.language.iso | eng | en_US |
dc.publisher | Wiley | en_US |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internasjonal | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/deed.no | * |
dc.title | A Scalable High-Yielding and Selective Oxidative Heck Cross-Coupling – A Key Step for the Synthesis of trans- Stilbenes | en_US |
dc.type | Journal article | en_US |
dc.type | Peer reviewed | en_US |
dc.description.version | publishedVersion | en_US |
dc.rights.holder | Copyright the authors 2021 | en_US |
cristin.ispublished | true | |
cristin.fulltext | original | |
cristin.qualitycode | 1 | |
dc.identifier.doi | 10.1002/ejoc.202100493 | |
dc.identifier.cristin | 1982581 | |
dc.source.journal | European Journal of Organic Chemistry | en_US |
dc.source.pagenumber | 5519-5529 | en_US |
dc.identifier.citation | European Journal of Organic Chemistry. 2021, 2021 (40), 5519-5529. | en_US |
dc.source.volume | 2021 | en_US |
dc.source.issue | 40 | en_US |