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A chemoenzymatic total synthesis of (+)-Clividine

White, Lorenzo; Schwartz, Brett; Banwell, Martin; Willis, Anthony

Description

The title compound, ent-1, the non-natural enantiomeric form of the lycorenine-type alkaloid (-)-clividine (1), has been prepared using the enantiomerically pure (ee >99.8%) cis-1,2-dihydrocatechol 3 as starting material. A key feature associated with the closing stages of the synthesis involved the diastereoselective addition of a nitrogen-centered radical onto a pendant cyclohexene to establish the cis-fused D-ring and the required stereochemistry at C11b in the final product ent-1.

dc.contributor.authorWhite, Lorenzo
dc.contributor.authorSchwartz, Brett
dc.contributor.authorBanwell, Martin
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-10T22:53:20Z
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/59309
dc.description.abstractThe title compound, ent-1, the non-natural enantiomeric form of the lycorenine-type alkaloid (-)-clividine (1), has been prepared using the enantiomerically pure (ee >99.8%) cis-1,2-dihydrocatechol 3 as starting material. A key feature associated with the closing stages of the synthesis involved the diastereoselective addition of a nitrogen-centered radical onto a pendant cyclohexene to establish the cis-fused D-ring and the required stereochemistry at C11b in the final product ent-1.
dc.publisherAmerican Chemical Society
dc.sourceJournal of Organic Chemistry
dc.subjectKeywords: Cyclohexenes; Diastereoselective additions; Key feature; Title compounds; Total synthesis; Olefins; Stereochemistry; Stereoselectivity; Enantiomers; alkaloid derivative; clividine; cyclohexene derivative; nitrogen; unclassified drug; article; chemical str
dc.titleA chemoenzymatic total synthesis of (+)-Clividine
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume76
dc.date.issued2011
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.ariespublicationu4005981xPUB484
local.type.statusPublished Version
local.contributor.affiliationWhite, Lorenzo, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationSchwartz, Brett, College of Physical and Mathematical Sciences, ANU
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.issue15
local.bibliographicCitation.startpage6250
local.bibliographicCitation.lastpage6257
local.identifier.doi10.1021/jo201005d
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T10:24:25Z
local.identifier.scopusID2-s2.0-79961076425
local.identifier.thomsonID000293252600039
CollectionsANU Research Publications

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