FORMAL SYNTHESIS OF THE JUGLOMYCINS

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dc.contributor.author Brimble, Margaret en
dc.contributor.author IRELAND, E en
dc.date.accessioned 2011-09-19T03:44:16Z en
dc.date.issued 1994-11-07 en
dc.identifier.citation J CHEM SOC PERK T 1 3109-3114 07 Nov 1994 en
dc.identifier.issn 0300-922X en
dc.identifier.uri http://hdl.handle.net/2292/8105 en
dc.description.abstract 5′-Deoxyjuglomycin A 3 and 5′-methoxyjuglomycin A 4 have been synthesized via oxidative fragmentation of furo[3,2-b]naphtho[2,1-d]furans 9 and 10 respectively. Addition of 2-trimethylsiloxyfuran 5 to naphthoquinone sulfides 7, 8 afforded the key adducts 9, 10 which then underwent fragmentation to the quinone sulfides 11, 14 using ceric ammonium nitrate. Treatment of the trimethylsilyl derivatives 13, 15 of the sulfides 11, 14 with meta-chloroperoxybenzoic acid effected conversion into the sulfoxides 16, 18 which then underwent smooth desulfurization using tributyltin hydride to the quinones 21, 23. Finally, hydrolysis of the trimethylsilyl group completed the synthesis of 5′-deoxyjuglomycin A 3 and 5′-methoxyjuglomycin A 4. en
dc.language English en
dc.publisher ROYAL SOC CHEMISTRY 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. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject Science & Technology en
dc.subject Physical Sciences en
dc.subject Chemistry, Organic en
dc.subject Chemistry en
dc.title FORMAL SYNTHESIS OF THE JUGLOMYCINS en
dc.type Journal Article en
dc.identifier.doi 10.1039/p19940003109 en
pubs.issue 21 en
pubs.begin-page 3109 en
dc.rights.holder Copyright: 1994 Royal Society of Chemistry en
pubs.author-url http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=A1994PQ66700011&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=6e41486220adb198d0efde5a3b153e7d en
pubs.end-page 3114 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 141819 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 2013-06-05 en


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