Show simple item record

dc.contributor.authorRankin, SSen_US
dc.contributor.authorCaldwell, JJen_US
dc.contributor.authorCronin, NBen_US
dc.contributor.authorvan Montfort, RLMen_US
dc.contributor.authorCollins, Ien_US
dc.date.accessioned2016-11-21T14:34:11Z
dc.date.issued2016-09en_US
dc.identifier.citationEuropean journal of organic chemistry, 2016, 2016 (26), pp. 4496 - 4507en_US
dc.identifier.issn1434-193Xen_US
dc.identifier.urihttps://repository.icr.ac.uk/handle/internal/220
dc.identifier.doi10.1002/ejoc.201600756en_US
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.en_US
dc.formatPrint-Electronicen_US
dc.format.extent4496 - 4507en_US
dc.languageengen_US
dc.language.isoengen_US
dc.titleSynthesis of a Ribose-Incorporating Medium Ring Scaffold via a Challenging Ring-Closing Metathesis Reaction.en_US
dc.typeJournal Article
dcterms.dateAccepted2016-07-21en_US
rioxxterms.versionofrecord10.1002/ejoc.201600756en_US
rioxxterms.licenseref.urihttps://creativecommons.org/licenses/by/4.0en_US
rioxxterms.licenseref.startdate2016-09en_US
rioxxterms.typeJournal Article/Reviewen_US
dc.relation.isPartOfEuropean journal of organic chemistryen_US
pubs.issue26en_US
pubs.notesNot knownen_US
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-statusPublisheden_US
pubs.volume2016en_US
pubs.embargo.termsNot knownen_US
icr.researchteamMedicinal Chemistry 2en_US
icr.researchteamHit Discovery & Structural Designen_US
dc.contributor.icrauthorCaldwell, Johnen_US
dc.contributor.icrauthorCollins, Ianen_US
dc.contributor.icrauthorVan Montfort, Roberten_US
dc.contributor.icrauthorRankin, Stuarten_US


Files in this item

Thumbnail
Thumbnail

This item appears in the following Collection(s)

Show simple item record