dc.contributor.author |
Meilert, Kai |
en |
dc.contributor.author |
Brimble, Margaret |
en |
dc.date.accessioned |
2011-09-21T22:35:57Z |
en |
dc.date.issued |
2006 |
en |
dc.identifier.citation |
Org Biomol Chem 4(11):2184-2192 07 Jun 2006 |
en |
dc.identifier.issn |
1477-0520 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8219 |
en |
dc.description.abstract |
The enantioselective synthesis of the bis-spiroacetal fragment of the shellfish toxins, spirolides B 1 and D 2, is reported. The carbon framework was constructed via a Barbier reaction of dihydropyran 10 with aldehyde 11, followed by two oxidative radical cyclizations to construct the bis-spiroacetal ring system. A silyl-modified Prins cyclization and enantioselective crotylation successfully installed the stereocenters in the cyclization precursor 21. The initial unsaturated bis-spiroacetals 9a–d underwent equilibration during epoxidation to trans-epoxide 24 that was converted to tertiary alcohol 7. |
en |
dc.language |
EN |
en |
dc.publisher |
ROYAL SOC CHEMISTRY |
en |
dc.relation.ispartofseries |
Organic & 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 |
SAKURAI ISMS REACTION |
en |
dc.subject |
RELATIVE STEREOCHEMISTRY |
en |
dc.subject |
COUPLING REACTION |
en |
dc.subject |
PINNA-MURICATA |
en |
dc.subject |
CHLORIDE |
en |
dc.subject |
CHEMISTRY |
en |
dc.subject |
CATALYSIS |
en |
dc.subject |
REAGENTS |
en |
dc.subject |
EPOXIDE |
en |
dc.subject |
ALKENES |
en |
dc.title |
Synthesis of the bis-spiroacetal moiety of the shellfish toxins spirolides B and D using an iterative oxidative radical cyclisation strategy |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1039/b604334h |
en |
pubs.issue |
11 |
en |
pubs.begin-page |
2184 |
en |
pubs.volume |
4 |
en |
dc.rights.holder |
Copyright: 2006 The Royal Society of Chemistry |
en |
dc.identifier.pmid |
16729128 |
en |
pubs.end-page |
2192 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
65000 |
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 |
16729128 |
en |