dc.contributor.author |
Sperry, Jonathan |
en |
dc.contributor.author |
Sejberg, Jimmy |
en |
dc.contributor.author |
Stiemke, Frank |
en |
dc.contributor.author |
Brimble, Margaret |
en |
dc.date.accessioned |
2011-09-18T23:56:38Z |
en |
dc.date.issued |
2009 |
en |
dc.identifier.citation |
Oraganic Biomolecular Chemistry 7:2599-2603 2009 |
en |
dc.identifier.issn |
1477-0520 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8022 |
en |
dc.description.abstract |
Studies towards the biomimetic synthesis of cardinalin 3 are described. Despite the successful enantioselective synthesis of the monomeric pyranonaphthoquinone ventiloquinone L, it subsequently failed to undergo a proposed biomimetic homodimerisation to cardinalin 3 using a range of oxidants. However, treatment of a related naphthopyran with cerium ammonium nitrate (CAN) facilitated a tandem biaryl bond formation–oxidative demethylation sequence furnishing a dimeric pyranonaphthoquinone that had exclusively dimerised at C6. The nature of this unusual sequence is discussed and the product subsequently converted to the C6 regioisomer of cardinalin 3. |
en |
dc.language |
EN |
en |
dc.publisher |
ROYAL SOC CHEMISTRY |
en |
dc.relation.ispartofseries |
Oraganic Biomolecular 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://www.sherpa.ac.uk/romeo/issn/1477-0520/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
DIMERIC PYRANONAPHTHOQUINONE CORE |
en |
dc.subject |
CERIUM(IV) AMMONIUM-NITRATE |
en |
dc.subject |
ENANTIOSELECTIVE SYNTHESIS |
en |
dc.subject |
VENTILOQUINONE-L |
en |
dc.subject |
ANNULATION |
en |
dc.subject |
REDUCTION |
en |
dc.subject |
QUINONE |
en |
dc.subject |
AGENTS |
en |
dc.title |
Biomimetic Studies Towards the Cardinalins: Synthesis of (+)-Ventiloquinone L and an Unusual Dimerisation |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1039/b905077a |
en |
pubs.issue |
12 |
en |
pubs.begin-page |
2599 |
en |
pubs.volume |
7 |
en |
dc.rights.holder |
Copyright: 2009 The Royal Society of Chemistry |
en |
dc.identifier.pmid |
19503935 |
en |
pubs.end-page |
2603 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
86200 |
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 |
2010-09-01 |
en |
pubs.dimensions-id |
19503935 |
en |