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dc.contributor.authorRankin, SS
dc.contributor.authorCaldwell, JJ
dc.contributor.authorCronin, NB
dc.contributor.authorvan Montfort, RLM
dc.contributor.authorCollins, I
dc.date.accessioned2016-11-21T14:34:11Z
dc.date.issued2016-09
dc.identifier.citationEuropean journal of organic chemistry, 2016, 2016 (26), pp. 4496 - 4507
dc.identifier.issn1434-193X
dc.identifier.urihttps://repository.icr.ac.uk/handle/internal/220
dc.identifier.doi10.1002/ejoc.201600756
dc.description.abstractA practical synthesis of a novel oxabicyclo[6.2.1]undecenetriol useful as a medicinal chemistry scaffold has been developed starting from l-ribose. The sequence involves an oxidation/Grignard addition sequence and a challenging ring-closing metathesis (RCM) reaction as the ring forming step. Exploration of the RCM substrate protecting groups revealed the key factor for successful nine-membered medium ring formation to be conformational bias of the reacting alkenes of the RCM substrate by very bulky silyl ether protecting groups. The synthesis also allowed access to an epimeric triol and saturated and unsaturated variants of the nine-membered ring. The medium ring conformation of the oxabicyclo[6.2.1]undecenetriol was determined by X-ray crystallography and correlated to the solution state conformation by NMR experiments.
dc.formatPrint-Electronic
dc.format.extent4496 - 4507
dc.languageeng
dc.language.isoeng
dc.rights.urihttps://creativecommons.org/licenses/by/4.0
dc.titleSynthesis of a Ribose-Incorporating Medium Ring Scaffold via a Challenging Ring-Closing Metathesis Reaction.
dc.typeJournal Article
dcterms.dateAccepted2016-07-21
rioxxterms.versionofrecord10.1002/ejoc.201600756
rioxxterms.licenseref.urihttps://creativecommons.org/licenses/by/4.0
rioxxterms.licenseref.startdate2016-09
rioxxterms.typeJournal Article/Review
dc.relation.isPartOfEuropean journal of organic chemistry
pubs.issue26
pubs.notesNot known
pubs.organisational-group/ICR
pubs.organisational-group/ICR/Primary Group
pubs.organisational-group/ICR/Primary Group/ICR Divisions
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Cancer Therapeutics
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Cancer Therapeutics/Hit Discovery & Structural Design
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Cancer Therapeutics/Medicinal Chemistry 2
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Structural Biology
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Structural Biology/Hit Discovery & Structural Design
pubs.organisational-group/ICR
pubs.organisational-group/ICR/Primary Group
pubs.organisational-group/ICR/Primary Group/ICR Divisions
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Cancer Therapeutics
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Cancer Therapeutics/Hit Discovery & Structural Design
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Cancer Therapeutics/Medicinal Chemistry 2
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Structural Biology
pubs.organisational-group/ICR/Primary Group/ICR Divisions/Structural Biology/Hit Discovery & Structural Design
pubs.publication-statusPublished
pubs.volume2016
pubs.embargo.termsNot known
icr.researchteamMedicinal Chemistry 2en_US
icr.researchteamHit Discovery & Structural Designen_US
dc.contributor.icrauthorRankin, Stuarten
dc.contributor.icrauthorCaldwell, Johnen
dc.contributor.icrauthorCollins, Ianen
dc.contributor.icrauthorVan Montfort, Roberten


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