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dc.contributor.authorRussell, David A
dc.contributor.authorFreudenreich, Julien J
dc.contributor.authorStewart, Hannah L
dc.contributor.authorBond, Andrew D
dc.contributor.authorSore, Hannah F
dc.contributor.authorSpring, David R
dc.date.accessioned2018-11-20T00:30:35Z
dc.date.available2018-11-20T00:30:35Z
dc.date.issued2018-09-11
dc.identifier.issn1477-0520
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/285443
dc.description.abstractWe describe semi-syntheses of the 11-hydroxyrotenoids sumatrol (1) and villosinol (2), starting from rotenone (5), using an oxime-directed C11-H functionalisation approach. Thus, rotenone (5) was converted into rotenone oxime (6), which gave dimeric palladacycle 7 following reaction with Na2PdCl4·3H2O. Controlled, divergent, oxidation of palladacycle 7 with either Pb(OAc)4 or K2Cr2O7 afforded the 11-acetoxylated intermediates 9 and 13, respectively, which were transformed into sumatrol (1) and villosinol (2).
dc.format.mediumPrint
dc.languageeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.titleSemi-syntheses of the 11-hydroxyrotenoids sumatrol and villosinol.
dc.typeArticle
prism.endingPage6398
prism.issueIdentifier35
prism.publicationDate2018
prism.publicationNameOrg Biomol Chem
prism.startingPage6395
prism.volume16
dc.identifier.doi10.17863/CAM.32803
dcterms.dateAccepted2018-08-21
rioxxterms.versionofrecord10.1039/c8ob01919c
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserved
rioxxterms.licenseref.startdate2018-09
dc.contributor.orcidBond, Andrew [0000-0002-1744-0489]
dc.contributor.orcidSore, Hannah [0000-0002-6542-0394]
dc.contributor.orcidSpring, David [0000-0001-7355-2824]
dc.identifier.eissn1477-0539
rioxxterms.typeJournal Article/Review
pubs.funder-project-idEngineering and Physical Sciences Research Council (EP/J016012/1)
pubs.funder-project-idEngineering and Physical Sciences Research Council (EP/P020291/1)
cam.issuedOnline2018
rioxxterms.freetoread.startdate2019-09-30


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