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From one to two quaternary centers : ester or nitrile α-alkylation applied to bioactive alkaloids
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dc.contributor.author | Voûte, Nicholas | |
dc.contributor.author | Neal, Andrew | |
dc.contributor.author | Medda, Federico | |
dc.contributor.author | Johnston, Craig A. | |
dc.contributor.author | Slawin, Alexandra M. Z. | |
dc.contributor.author | Westwood, Nicholas J. | |
dc.date.accessioned | 2019-11-08T00:36:51Z | |
dc.date.available | 2019-11-08T00:36:51Z | |
dc.date.issued | 2018-11-08 | |
dc.identifier | 256418704 | |
dc.identifier | 0c1f1bd8-5b25-41fa-a85c-8e6942ec9834 | |
dc.identifier | 85056402899 | |
dc.identifier | 000453621800004 | |
dc.identifier.citation | Voûte , N , Neal , A , Medda , F , Johnston , C A , Slawin , A M Z & Westwood , N J 2018 , ' From one to two quaternary centers : ester or nitrile α-alkylation applied to bioactive alkaloids ' , Tetrahedron , vol. In press . https://doi.org/10.1016/j.tet.2018.10.077 | en |
dc.identifier.issn | 0040-4020 | |
dc.identifier.other | ORCID: /0000-0003-0630-0138/work/56424167 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861722 | |
dc.identifier.uri | https://hdl.handle.net/10023/18883 | |
dc.description | The authors would like to acknowledge EPSRC for PhD funding through the Doctoral Training Schemes. | en |
dc.description.abstract | The synthesis of all-carbon quaternary centers remains a challenge. Here we describe studies on the formation of two adjacent all-carbon quaternary centers in the context of the planned synthesis of the bioactive natural products perophoramidine and the communesins. In one approach the key step involves ester-alkylation using either allyl bromide or formaldehyde as the electrophile. An unexpected rapid auto-oxidation reaction during the synthesis of the alkylation substrates limited the scalability of this approach. In a second route, alkylation of a nitrile-containing precursor was planned. The use of the TosMIC reagent on a complex substrate gave the nitrile for alkylation. The assignment of the relative stereochemistry of the products was done through the extensive use of small molecule X-ray crystallography. | |
dc.format.extent | 1171359 | |
dc.language.iso | eng | |
dc.relation.ispartof | Tetrahedron | en |
dc.subject | Dehaloperophoramidine | en |
dc.subject | Diastereoselective | en |
dc.subject | Quaternary | en |
dc.subject | Stereocenter | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | From one to two quaternary centers : ester or nitrile α-alkylation applied to bioactive alkaloids | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | 10.1016/j.tet.2018.10.077 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-11-08 |
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