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Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D
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dc.contributor.author | Aitken, R. Alan | |
dc.contributor.author | Murray, Lorna | |
dc.date.accessioned | 2018-09-26T23:45:54Z | |
dc.date.available | 2018-09-26T23:45:54Z | |
dc.date.issued | 2017-11-15 | |
dc.identifier | 251160765 | |
dc.identifier | edab32e3-ba12-4ce0-b701-592f9adfdd18 | |
dc.identifier | 85030846195 | |
dc.identifier | 000415770700003 | |
dc.identifier.citation | Aitken , R A & Murray , L 2017 , ' Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D ' , Tetrahedron Letters , vol. 58 , no. 46 , pp. 4328-4332 . https://doi.org/10.1016/j.tetlet.2017.09.073 | en |
dc.identifier.issn | 0040-4039 | |
dc.identifier.other | ORCID: /0000-0001-6959-5311/work/37255565 | |
dc.identifier.uri | https://hdl.handle.net/10023/16083 | |
dc.description | The authors thank EPSRC (UK) for a DTA studentship (Grant No. EP/P501768/1). | en |
dc.description.abstract | Six stabilised phosphonium ylides bearing ortho-benzylaminophenyl and cinnamoyl (or a heterocyclic analogue) groups have been prepared and upon flash vacuum pyrolysis at 800 °C were found to undergo cascade cyclization processes to give mainly 3-styrylquinolines but also in some cases ring-fused carbazoles and other fused-ring heterocyclic products. By starting with an appropriate ring-methylated precursor the natural product Eustifoline D was obtained in 19% yield in the pyrolysis in addition to the 3-(2-furylethenyl)quinoline (46%). | |
dc.format.extent | 5 | |
dc.format.extent | 430909 | |
dc.language.iso | eng | |
dc.relation.ispartof | Tetrahedron Letters | en |
dc.subject | Cyclization | en |
dc.subject | Gas-phase reaction | en |
dc.subject | Phosphorus ylides | en |
dc.subject | Fused-ring systems | en |
dc.subject | Radical reaction | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1016/j.tetlet.2017.09.073 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2018-09-27 |
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