Rapid and Enantioselective Assembly of the Lycorine Framework Using Chemoenzymatic Techniques

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dc.contributor.authorJones, Matthew
dc.contributor.authorSchwartz, Brett
dc.contributor.authorWillis, Anthony
dc.contributor.authorBanwell, Martin
dc.date.accessioned2015-12-10T22:30:57Z
dc.date.issued2009
dc.date.updated2016-02-24T10:23:05Z
dc.description.abstractThe pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/1885/55316
dc.publisherAmerican Chemical Society
dc.sourceOrganic Letters
dc.subjectKeywords: Amaryllidaceae alkaloid; bromobenzene; enzyme; lycorine; nitrobenzoic acid derivative; phenanthridine derivative; article; chemistry; metabolism; synthesis; X ray crystallography; Amaryllidaceae Alkaloids; Bromobenzenes; Crystallography, X-Ray; Enzymes; N
dc.titleRapid and Enantioselective Assembly of the Lycorine Framework Using Chemoenzymatic Techniques
dc.typeJournal article
local.bibliographicCitation.issue15
local.bibliographicCitation.lastpage3509
local.bibliographicCitation.startpage3506
local.contributor.affiliationJones, Matthew, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationSchwartz, Brett, 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.authoremailu4691352@anu.edu.au
local.contributor.authoruidJones, Matthew, u4193049
local.contributor.authoruidSchwartz, Brett, u4691352
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.ariespublicationu4005981xPUB325
local.identifier.citationvolume11
local.identifier.doi10.1021/ol901364n
local.identifier.scopusID2-s2.0-68149142567
local.identifier.thomsonID000268479900087
local.identifier.uidSubmittedByu4005981
local.type.statusPublished Version

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