dc.contributor.author |
Gueret, Stephanie |
en |
dc.contributor.author |
Boyd, Peter |
en |
dc.contributor.author |
Brimble, Margaret |
en |
dc.date.accessioned |
2011-09-06T02:10:42Z |
en |
dc.date.issued |
2010 |
en |
dc.identifier.citation |
Acta Crystallogr Sect E Struct Rep Online 66(Pt 7):o1778-o1779 2010 |
en |
dc.identifier.issn |
1600-5368 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/7710 |
en |
dc.description.abstract |
The crystal structure of the title compound, C34H54N2O4, has been solved in order to prove the relative and absolute chirality of the newly-formed stereocentres which were established using an asymmetric Diels-Alder reaction at an earlier stage in the synthesis. This unprecedented stable dialdimine contains a 14-membered ring and was obtained as the minor diastereoisomer in the Diels-Alder reaction. The absolute stereochemistry of the stereocentres of the acetal functionality was known to be R based on the use of a chiral (R)-trisubstituted dienophile derived from enantiopure (S)glyceraldehyde. The assignment of the configuration in the dienophile and the title di-aldimine differs from (S)-glyceraldehyde due to a change in the priority order of the substituents. The crystal structure establishes the presence of six stereocentres all attributed to be R. The 14-membered ring contains two aldimine bonds [C-N = 1.258 (2) and 1.259 (2) angstrom]. It adopts a similar conformation to that proposed for trans-trans-cyclotetradeca-1,8-dienes. |
en |
dc.language |
EN |
en |
dc.publisher |
WILEY-BLACKWELL PUBLISHING, INC |
en |
dc.relation.ispartofseries |
ACTA CRYSTALLOGR E |
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/1600-5368/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.rights.uri |
http://journals.iucr.org/services/copyrightpolicy.html |
en |
dc.subject |
SHELLFISH |
en |
dc.subject |
TOXINS |
en |
dc.title |
(1R,6R,13R,18R)-(Z,Z)-1,18-Bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,16-dimethylene-8,20-diazadispiro[5.6.5.6]tetracosa-7,19-diene |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1107/S1600536810023998 |
en |
pubs.issue |
7 |
en |
pubs.begin-page |
O1778 |
en |
pubs.volume |
E66 |
en |
dc.rights.holder |
Copyright: International Union of Crystallography |
en |
dc.identifier.pmid |
21587991 |
en |
pubs.end-page |
o1779 |
en |
pubs.publication-status |
Published |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/OpenAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
119830 |
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 |
2010-09-28 |
en |
pubs.dimensions-id |
21587991 |
en |