New natural products in the discorhabdin A- and B-series from New Zealand-sourced Latrunculia spp. sponges

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dc.contributor.author Grkovic, Tanja en
dc.contributor.author Copp, Brent en
dc.date.accessioned 2017-10-23T23:58:57Z en
dc.date.available 2009-06-04 en
dc.date.issued 2009-08-08 en
dc.identifier.citation Tetrahedron, 65(32):6335-6340, 08 Aug 2009 en
dc.identifier.issn 0040-4020 en
dc.identifier.uri http://hdl.handle.net/2292/36201 en
dc.description.abstract A survey of the secondary metabolite chemistry profiles of New Zealand sponges of the genus Latrunculia has yielded new members of the discorhabdin A- and B-type families. The structure elucidation of (+)-(6R,8S)-1-thiomethyldiscorhabdin G∗/I (5) and both enantiomers of 16a,17a-dehydrodiscorhabdin W (6) are reported. Absolute configurations were assigned by comparison with a dataset of recently reported electronic circular dichroism spectra of discorhabdin alkaloids. A stereochemical correction of the recently reported natural product (+)-3-dihydrodiscorhabdin A from (3S,5R,6S,8S)-(7) to the C3-epimeric (+)-(3R,5R,6S,8S)-(8) and assignment of absolute configuration is also presented. Semi-synthesis of (+)-(3S,5R,6S,8S)-(7) from (+)-discorhabdin A provided further evidence for this structure revision. Cytotoxicity data is reported for 5–8. en
dc.language English en
dc.publisher Elsevier 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. Details obtained from http://sherpa.ac.uk/romeo/issn/0040-4020/ https://www.elsevier.com/about/our-business/policies/sharing en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title New natural products in the discorhabdin A- and B-series from New Zealand-sourced Latrunculia spp. sponges en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.tet.2009.06.012 en
pubs.issue 32 en
pubs.begin-page 6335 en
pubs.volume 65 en
dc.rights.holder Copyright: Elsevier en
pubs.author-url http://www.sciencedirect.com/science/article/pii/S0040402009008564 en
pubs.end-page 6340 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 93306 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 1464-5416 en
pubs.record-created-at-source-date 2010-09-01 en
pubs.online-publication-date 2009-06-10 en


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