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Polycyclic ethers and an unexpected dearomatisation reaction during studies towards the bioactive alkaloid, perophoramidine
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dc.contributor.author | Johnston, Craig A. | |
dc.contributor.author | Wilkie, Ross P. | |
dc.contributor.author | Krauss, Helmut | |
dc.contributor.author | Neal, Andrew R. | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Lebl, Tomas | |
dc.contributor.author | Westwood, Nicholas J. | |
dc.date.accessioned | 2019-04-27T23:38:00Z | |
dc.date.available | 2019-04-27T23:38:00Z | |
dc.date.issued | 2018-06-28 | |
dc.identifier | 252962799 | |
dc.identifier | c4c3e126-3b92-41a0-ad0e-ee4f7a25be35 | |
dc.identifier | 85046716910 | |
dc.identifier | 000436222800020 | |
dc.identifier.citation | Johnston , C A , Wilkie , R P , Krauss , H , Neal , A R , Slawin , A M Z , Lebl , T & Westwood , N J 2018 , ' Polycyclic ethers and an unexpected dearomatisation reaction during studies towards the bioactive alkaloid, perophoramidine ' , Tetrahedron , vol. 74 , no. 26 , pp. 3339-3347 . https://doi.org/10.1016/j.tet.2018.04.086 | en |
dc.identifier.issn | 0040-4020 | |
dc.identifier.other | RIS: urn:C8B01E54498090F03FE29710886A40B3 | |
dc.identifier.other | ORCID: /0000-0002-0269-3221/work/48131696 | |
dc.identifier.other | ORCID: /0000-0003-0630-0138/work/56424200 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56862014 | |
dc.identifier.uri | https://hdl.handle.net/10023/17598 | |
dc.description | We would like to acknowledge EPSRC for PhD funding through the Doctoral Training Schemes and the EPSRC National Mass Spectrometry Service Centre, Swansea for mass spectrometric analysis. | en |
dc.description.abstract | The bioactive alkaloid natural product perophoramidine and the related family of compounds known as the communesins have inspired the synthesis community for more than a decade. Many of the elegant approaches have required the synthesis of complex intermediates that have not always reacted in the expected manner. In this study we describe a series of cyclic ether-containing precursors that were prepared during our synthetic studies towards these natural products. Attempts to open the cyclic ether ring and trap the resulting stabilised carbocation with a carbon nucleophile ultimately led to the preparation of a diallyl-substituted all carbon quaternary centre. Subsequent attempts to differentiate between the two allyl groups resulted in a relatively clean transformation to an unexpected compound. Extensive structural characterisation, including small molecule X-ray crystallography, showed that a dearomatisation reaction had occurred. | |
dc.format.extent | 834082 | |
dc.language.iso | eng | |
dc.relation.ispartof | Tetrahedron | en |
dc.subject | Natural product | en |
dc.subject | Ring opening reaction | en |
dc.subject | Cyclic ether | en |
dc.subject | Dearomatisation | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Polycyclic ethers and an unexpected dearomatisation reaction during studies towards the bioactive alkaloid, perophoramidine | 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.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.1016/j.tet.2018.04.086 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-04-28 |
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