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A chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin

Chang, Ee; Schwartz, Brett; Draffan, Alistair; Banwell, Martin; Willis, Anthony

Description

The natural product (-)-platencin is a potent antibacterial agent that exerts its effects through a novel mode of action. As such, it is an important lead in the development of next-generation antibacterials that are urgently needed because of the rapidly developing resistance to current therapies. The work reported here concerns the development of a convergent and chemoenzymatic total synthesis of (-)-platencin by methods that should provide access to a range of biologically relevant...[Show more]

dc.contributor.authorChang, Ee
dc.contributor.authorSchwartz, Brett
dc.contributor.authorDraffan, Alistair
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-10T23:12:30Z
dc.identifier.issn1861-4728
dc.identifier.urihttp://hdl.handle.net/1885/64018
dc.description.abstractThe natural product (-)-platencin is a potent antibacterial agent that exerts its effects through a novel mode of action. As such, it is an important lead in the development of next-generation antibacterials that are urgently needed because of the rapidly developing resistance to current therapies. The work reported here concerns the development of a convergent and chemoenzymatic total synthesis of (-)-platencin by methods that should provide access to a range of biologically relevant analogues. The key step involves a thermally promoted and facially selective intramolecular Diels-Alder (IMDA) cycloaddition reaction to give an adduct that embodies the tricarbocyclic core of (-)-platencin. This adduct was elaborated over thirteen steps to the natural product. The substrate for the IMDA reaction was prepared by Stille cross-coupling of a Z-configured alkenylstannane with an iodinated diene obtained in an enantiomerically pure form through the whole-cell biotransformation of iodobenzene.
dc.publisherWiley-VCH Verlag GMBH
dc.sourceChemistry - An Asian Journal
dc.titleA chemoenzymatic and fully stereocontrolled total synthesis of the antibacterial natural product (-)-platencin
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume10
dc.date.issued2015
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB877
local.type.statusPublished Version
local.contributor.affiliationChang, Ee, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationSchwartz, Brett, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationDraffan, Alistair, Biota Holdings Limited
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue2
local.bibliographicCitation.startpage427
local.bibliographicCitation.lastpage439
local.identifier.doi10.1002/asia.201403069
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2015-12-10T09:30:54Z
local.identifier.scopusID2-s2.0-84921633272
CollectionsANU Research Publications

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