gem -Dihalogenocyclopropanes as building blocks in natural product synthesis: enantioselective total syntheses of ent -erythramine and 3- epi -erythramine

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dc.contributor.authorStanislawski, Pauline
dc.contributor.authorWillis, Anthony
dc.contributor.authorBanwell, Martin
dc.date.accessioned2015-12-08T22:25:24Z
dc.date.issued2007
dc.date.updated2015-12-08T09:05:22Z
dc.description.abstractent-Erythramine ((-)-1), the enantiomer of the alkaloid erythramine, was prepared in 15 steps from known compounds. The first of three pivotal bond-forming steps in the synthesis was a Suzuki-Miyaura cross-coupling reaction of the starting materials to give a bis-silyl ether. The second involved silver(I)-induced electrocyclic ring opening of the gem-dichlorocyclo-propane formed in the next step and trapping of the ensuing π-allyl cation by the tethered nitrogen atom to give, following cleavage of the allyloxycarbonyl protecting group, an approximately 5:6 mixture of the chromatographically separable diastereoisomeric spirocyclic products. In the third critical bond-forming reaction, the iodide formed from one of the diastereoisomers underwent a radical-addition/ elimination reaction sequence that led to (-)-1 in 89% yield. The application of the same sequence of transformations to the other diastereoisomer afforded 3-epi-(+)-erythramine (3-epi-(+)-1).
dc.identifier.issn1861-4728
dc.identifier.urihttp://hdl.handle.net/1885/33413
dc.publisherWiley-VCH Verlag GMBH
dc.sourceChemistry - An Asian Journal
dc.subjectKeywords: 1,3 benzodioxole derivative; biological product; cyclopropane derivative; erythramine; isoquinoline derivative; nitrogen; unclassified drug; article; chemistry; infrared spectroscopy; liquid chromatography; mass spectrometry; nuclear magnetic resonance sp Alkaloids; Cyclopropanes; Radical reactions; Spirocyclization; Total synthesis
dc.titlegem -Dihalogenocyclopropanes as building blocks in natural product synthesis: enantioselective total syntheses of ent -erythramine and 3- epi -erythramine
dc.typeJournal article
local.bibliographicCitation.issue9
local.bibliographicCitation.lastpage1136
local.bibliographicCitation.startpage1127
local.contributor.affiliationStanislawski, Pauline, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.authoremailu8512028@anu.edu.au
local.contributor.authoruidStanislawski, Pauline, u3935273
local.contributor.authoruidWillis, Anthony, u8512028
local.contributor.authoruidBanwell, Martin, u9500594
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB102
local.identifier.citationvolume2
local.identifier.doi10.1002/asia.200700155
local.identifier.scopusID2-s2.0-34548559498
local.identifier.uidSubmittedByu4005981
local.type.statusPublished Version

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