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 |