Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach

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dc.contributor.author Dittrich, N en
dc.contributor.author Pilkington, Lisa en
dc.contributor.author Leung, Yee Fun en
dc.contributor.author Barker, David en
dc.date.accessioned 2017-07-02T21:56:39Z en
dc.date.issued 2017-04 en
dc.identifier.citation Tetrahedron 73:1881-1894 Article number 14 Apr 2017 en
dc.identifier.issn 0040-4020 en
dc.identifier.uri http://hdl.handle.net/2292/33921 en
dc.description.abstract Lamellarin K is a complex pyrrole natural product and member of the lamellarin family – a group of natural products known for their potent biological activities, such as, antiproliferative activity and inhibition of P-gp mediated drug efflux pumps. We herein describe the synthesis of the N-benzyl-des-D ring analogue of lamellarin K using a route that centres on an acyl-Claisen reaction to eventually prepare a highly-functionalised 1-aryl-4-methyl-1,4-diketone. Paal-Knorr pyrrole formation using this diketone undergoes auto-oxidation to give a fully-substituted 5-formyl pyrrole which was converted into the natural lactone B ring. Antiproliferative testing of the N-benzyl-des-D ring analogue gave an IC50 of 2.63 μM against the MDA-MB-231 breast cancer cell line. en
dc.publisher Pergamon Press Ltd. en
dc.relation.ispartofseries Tetrahedron 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.title Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.tet.2017.02.044 en
pubs.begin-page 1881 en
pubs.volume 73 en
dc.rights.holder Copyright: Elsevier en
pubs.end-page 1894 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 616590 en
pubs.org-id Medical and Health Sciences en
pubs.org-id Medical Sciences en
pubs.org-id Auckland Cancer Research en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.number 14 en
pubs.record-created-at-source-date 2017-07-01 en


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