dc.contributor.author |
Khalil, IM |
en |
dc.contributor.author |
Barker, David |
en |
dc.contributor.author |
Copp, Brent |
en |
dc.date.accessioned |
2017-07-26T02:22:48Z |
en |
dc.date.issued |
2015-12-07 |
en |
dc.identifier.citation |
Journal of Organic Chemistry, 81(1):282-289, 07 Dec 2015 |
en |
dc.identifier.issn |
0022-3263 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/34510 |
en |
dc.description.abstract |
Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K3[Fe(CN)6] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyamphimedine and amphimedine. |
en |
dc.format.medium |
Print-Electronic |
en |
dc.language |
English |
en |
dc.publisher |
American Chemical Society |
en |
dc.relation.ispartofseries |
Journal of Organic Chemistry |
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://sherpa.ac.uk/romeo/issn/0022-3263/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
Alkaloids |
en |
dc.subject |
Acridines |
en |
dc.subject |
Phenanthrolines |
en |
dc.subject |
Biological Products |
en |
dc.subject |
Molecular Structure |
en |
dc.title |
Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1021/acs.joc.5b02312 |
en |
pubs.issue |
1 |
en |
pubs.begin-page |
282 |
en |
pubs.volume |
81 |
en |
dc.identifier.pmid |
26642369 |
en |
pubs.author-url |
http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b02312 |
en |
pubs.end-page |
289 |
en |
pubs.publication-status |
Published |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
515395 |
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 |
dc.identifier.eissn |
1520-6904 |
en |
pubs.record-created-at-source-date |
2017-07-26 |
en |
pubs.dimensions-id |
26642369 |
en |