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dc.contributor.authorEl-Deeb, Ibrahim M
dc.contributor.authorRose, Faith J
dc.contributor.authorHealy, Peter C
dc.contributor.authorvon Itzstein, Mark
dc.date.accessioned2017-05-03T15:59:04Z
dc.date.available2017-05-03T15:59:04Z
dc.date.issued2014
dc.identifier.issn1477-0520
dc.identifier.doi10.1039/C4OB00842A
dc.identifier.urihttp://hdl.handle.net/10072/64127
dc.description.abstractAn improved and versatile synthesis of tafuramycin A, a potent anticancer and parasite-attenuating agent, is reported. The three major improvements that optimized yield, simplified purification and allowed the synthesis of more versatile duocarmycin analogues are: a first-time reported regioselective bromination using DMAP as catalyst; the control of the aryl radical alkene cyclization step to prevent the dechlorination side reaction; and the design of a new protection/deprotection method to avoid furan double bond reduction during the classical O-benzyl deprotection in the final step. This alternative protection/deprotection strategy provides ready access to duocarmycin seco-analogues that carry labile functionalities under reducing reaction conditions. Tafuramycin A (3) was prepared in either 8 steps from intermediate 6 or 7 steps from intermediate 17 in 52% or 37% yield respectively. Our strategy provides a significant improvement on the original procedure (11% overall yield) and greater versatility for analogue development.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherRSC Publications
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom4260
dc.relation.ispartofpageto4264
dc.relation.ispartofissue24
dc.relation.ispartofjournalOrganic & Biomolecular Chemistry
dc.relation.ispartofvolume12
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchOrganic chemical synthesis
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode340503
dc.titleA versatile synthesis of "tafuramycin A": A potent anticancer and parasite attenuating agent
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyGriffith Sciences, School of Natural Sciences
gro.hasfulltextNo Full Text
gro.griffith.authorHealy, Peter C.
gro.griffith.authorvon Itzstein, Mark
gro.griffith.authorRose, Faith J.
gro.griffith.authorEl-Deeb, Ibrahim Mustafa


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