SYNTHESIS OF THE INSECT FEEDING DETERRENT PERAMINE VIA MICHAEL ADDITION OF A PYRROLE ANION TO A NITROALKENE

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dc.contributor.author Brimble, Margaret en
dc.contributor.author ROWAN, DD en
dc.date.accessioned 2011-09-21T22:43:01Z en
dc.date.issued 1990-02-01 en
dc.identifier.citation J CHEM SOC PERK T 1 311-314 Feb 1990 en
dc.identifier.issn 0300-922X en
dc.identifier.uri http://hdl.handle.net/2292/8223 en
dc.description.abstract A total synthesis of peramine (1), the major insect feeding deterrent isolated from perennial ryegrass (Lolium perenne L.) infected with the endophytic fungus Acremonium lolii is reported. The key step involves the Michael addition of the potassium salt of methyl pyrrole-2-carboxylate (3) to the nitroalkene (4) providing access to a 3-substituted pyrrolo[1,2-a]pyrazin-1 (2H)-one (10). Displacement of the allylic bromide (11) by cyanomethyl cuprate provided the methodology for introducing the desired monosubstituted guanidino group via the nitrite (12). 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 SYNTHESIS OF THE INSECT FEEDING DETERRENT PERAMINE VIA MICHAEL ADDITION OF A PYRROLE ANION TO A NITROALKENE en
dc.type Journal Article en
dc.identifier.doi 10.1039/p19900000311 en
pubs.issue 2 en
pubs.begin-page 311 en
dc.rights.holder Copyright: Royal Society of Chemistry en
pubs.author-url http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=A1990CQ09200016&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=6e41486220adb198d0efde5a3b153e7d en
pubs.end-page 314 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 141835 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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