Modular total syntheses of the marine-derived resorcylic acid lactones cochliomycins A and B using a late-stage Nozaki-Hiyama-Kishi macrocyclization reaction

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dc.contributor.authorBolte, Benoit
dc.contributor.authorBasutto, Jose
dc.contributor.authorBryan, Christopher
dc.contributor.authorGarson, Mary J
dc.contributor.authorBanwell, Martin
dc.contributor.authorWard, James
dc.date.accessioned2015-12-10T23:12:05Z
dc.date.issued2015
dc.date.updated2015-12-10T09:26:33Z
dc.description.abstractThe natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/63955
dc.publisherAmerican Chemical Society
dc.sourceJournal of Organic Chemistry
dc.titleModular total syntheses of the marine-derived resorcylic acid lactones cochliomycins A and B using a late-stage Nozaki-Hiyama-Kishi macrocyclization reaction
dc.typeJournal article
local.bibliographicCitation.issue1
local.bibliographicCitation.lastpage470
local.bibliographicCitation.startpage460
local.contributor.affiliationBolte, Benoit, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBasutto, Jose, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBryan, Christopher, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationGarson, Mary J, University of Queensland
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWard, James, College of Physical and Mathematical Sciences, ANU
local.contributor.authoremailu5403288@anu.edu.au
local.contributor.authoruidBolte, Benoit, u5403288
local.contributor.authoruidBasutto, Jose, u4281352
local.contributor.authoruidBryan, Christopher, u4999088
local.contributor.authoruidBanwell, Martin, u9500594
local.contributor.authoruidWard, James, u4431856
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationu4005981xPUB868
local.identifier.citationvolume80
local.identifier.doi10.1021/jo5024602
local.identifier.scopusID2-s2.0-84928881167
local.identifier.uidSubmittedByu4005981
local.type.statusPublished Version

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