C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: synthesis of naphthyl-substituted 3,6-dioxabicyclo[3.2.2]nonanes

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dc.contributor.author Brimble, MA en
dc.contributor.author Brenstrum, Timothy en
dc.date.accessioned 2011-09-19T01:44:50Z en
dc.date.issued 2001 en
dc.identifier.citation Journal of the Chemical Society, Perkin Transactions 1 (14): 1612-1623 2001 en
dc.identifier.issn 1470-4358 en
dc.identifier.uri http://hdl.handle.net/2292/8065 en
dc.description.abstract The syntheses of naphthol 7, naphthol 8, naphthol 11 and naphthol 12 are described, starting from juglone 13. C-Glycosylation of naphthol 8 with benzyl-protected glycosyl donor 10 using trimethylsilyl trifluoromethanesulfonate and silver perchlorate or boron trifluoride–diethyl ether affords rearranged product 36 in which the glycosyl donor has undergone an unusual 1,6-hydride shift. Use of the corresponding naphthol 12 as the glycosyl acceptor under the same conditions affords the expected C-glycoside 34. Use of the naphthol 7 and naphthol 11 affords predominantly rearranged products 35 and 37 respectively, albeit in much lower yield than the reactions using the corresponding bromonaphthols. The study described herein establishes that introduction of an acetyl group to C-3, as in C-glycosylnaphthoquinone 4, as required for conversion to analogues of medermycin 1 such as 3, necessitates that the C-glycosylation step be effected before regioselective introduction of the acetyl group. en
dc.language EN en
dc.relation.ispartofseries Journal of the Chemical Society, Perkin Transactions 1 en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/1472-7781/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject LACTOQUINOMYCIN en
dc.subject GLYCOSIDES en
dc.subject MEDERMYCIN en
dc.subject KALAFUNGIN en
dc.subject SUGARS en
dc.title C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: synthesis of naphthyl-substituted 3,6-dioxabicyclo[3.2.2]nonanes en
dc.type Journal Article en
dc.identifier.doi 10.1039/B102807N en
pubs.issue 14 en
pubs.begin-page 1612 en
dc.rights.holder Copyright: 2001 Royal Society of Chemistry en
pubs.end-page 1623 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 3797 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en


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