Skip navigation
Skip navigation

A Total Synthesis of the Marine Alkaloid Discoipyrrole D

Zhang, Yiwen; Banwell, Martin

Description

A total synthesis of the diastereoisomeric pair of compounds, 4, assigned to the marine alkaloid discoipyrrole D is reported. A series of palladium-catalyzed cross-coupling and other reactions was employed to assemble the relevant 1,2,3,4-tetrasubstituted pyrrole (16) that was engaged in MoOPH-mediated oxidative cyclization, then conjugate addition, and redox processes to complete the synthesis. This work serves to confirm the structure (4) originally assigned to discoipyrrole D.

dc.contributor.authorZhang, Yiwen
dc.contributor.authorBanwell, Martin
dc.date.accessioned2021-05-04T01:22:28Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/231418
dc.description.abstractA total synthesis of the diastereoisomeric pair of compounds, 4, assigned to the marine alkaloid discoipyrrole D is reported. A series of palladium-catalyzed cross-coupling and other reactions was employed to assemble the relevant 1,2,3,4-tetrasubstituted pyrrole (16) that was engaged in MoOPH-mediated oxidative cyclization, then conjugate addition, and redox processes to complete the synthesis. This work serves to confirm the structure (4) originally assigned to discoipyrrole D.
dc.description.sponsorshipWe thank the Australian Research Council for financial support. Y.Z. is the grateful recipient of a PhD Scholarship provided by the China Scholarship Council of the People’s Republic of China. Dr. Hideki Onagi is thanked for his expert assistance with HPLC purifications and analyses.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherAmerican Chemical Society
dc.rights© 2017 American Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleA Total Synthesis of the Marine Alkaloid Discoipyrrole D
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume82
dc.date.issued2017
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4351680xPUB150
local.publisher.urlhttp://pubs.acs.org/journal/joceah/about.html
local.type.statusAccepted Version
local.contributor.affiliationZhang, Yiwen, College of Science, ANU
local.contributor.affiliationBanwell, Martin, College of Science, ANU
local.bibliographicCitation.issue18
local.bibliographicCitation.startpage9328
local.bibliographicCitation.lastpage9334
local.identifier.doi10.1021/acs.joc.7b01192
dc.date.updated2020-11-23T10:08:39Z
local.identifier.scopusID2-s2.0-85029539205
local.identifier.thomsonID000411304500008
dcterms.accessRightsOpen Access
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7797..."The Accepted Version can be archived in a Non-Commercial Institutional Repository If Required by Funder, If Required by Institution. 12 months embargo " from SHERPA/RoMEO site (as at 10/05/2021). This document is the Accepted Manuscript version of a Published Work that appeared in final form in [Journal of Organic Chemistry], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.joc.7b01192
CollectionsANU Research Publications

Download

File Description SizeFormat Image
A Total Synthesis of Discoipyrrole D Final.pdf432.23 kBAdobe PDFThumbnail


Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.

Updated:  19 May 2020/ Responsible Officer:  University Librarian/ Page Contact:  Library Systems & Web Coordinator