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Syntheses of Showdomycin and its Anomer Using N -(Triisopropylsilyl)pyrrole as a Synthetic Equivalent for the Maleimide C3-Anion

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dc.contributor.authorHungerford, Natasha
dc.contributor.authorArmitt, David
dc.contributor.authorBanwell, Martin
dc.date.accessioned2015-12-13T23:06:00Z
dc.date.available2015-12-13T23:06:00Z
dc.date.issued2003
dc.date.updated2015-12-12T08:03:13Z
dc.description.abstractShowdomycin (1) and its anomer (2) have been prepared in four steps from readily available trichloroacetimidate 9. The key step involves reaction of the last compound with the title pyrrole 3 so as to form a chromatographically separable mixture of the pyrrole C-glycosides 10 and 11. These pyrroles are desilylated then oxidized to the corresponding maleimides using PCC.
dc.identifier.issn0039-7881
dc.identifier.urihttp://hdl.handle.net/1885/85817
dc.publisherGeorg Thieme Verlag
dc.sourceSynthesis
dc.subjectKeywords: Anomers; Chromatographic analysis; Mixtures; Nitrogen compounds; Synthesis (chemical); anion; maleimide; n (triisopropylsilyl)pyrrole; pyrrole derivative; showdomycin; unclassified drug; article; chemical reaction; drug structure; drug synthesis; isomer; C-glycosides; Maleimides; Nucleosides; Oxidation; Pyrroles; Trichloroacetimidates
dc.titleSyntheses of Showdomycin and its Anomer Using N -(Triisopropylsilyl)pyrrole as a Synthetic Equivalent for the Maleimide C3-Anion
dc.typeJournal article
local.bibliographicCitation.issue12
local.bibliographicCitation.lastpage1843
local.bibliographicCitation.startpage1837
local.contributor.affiliationHungerford, Natasha, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationArmitt, David, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.authoruidHungerford, Natasha, u4047231
local.contributor.authoruidArmitt, David, v000225
local.contributor.authoruidBanwell, Martin, u9500594
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub14476
local.identifier.scopusID2-s2.0-0141742441
local.type.statusPublished Version

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