A chemoenzymatic total synthesis of (+)-Clividine
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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.author | White, Lorenzo | |
---|---|---|
dc.contributor.author | Schwartz, Brett | |
dc.contributor.author | Banwell, Martin | |
dc.contributor.author | Willis, Anthony | |
dc.date.accessioned | 2015-12-10T22:53:20Z | |
dc.identifier.issn | 0022-3263 | |
dc.identifier.uri | http://hdl.handle.net/1885/59309 | |
dc.description.abstract | 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.publisher | American Chemical Society | |
dc.source | Journal of Organic Chemistry | |
dc.subject | Keywords: 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.title | A chemoenzymatic total synthesis of (+)-Clividine | |
dc.type | Journal article | |
local.description.notes | Imported from ARIES | |
local.identifier.citationvolume | 76 | |
dc.date.issued | 2011 | |
local.identifier.absfor | 030502 - Natural Products Chemistry | |
local.identifier.ariespublication | u4005981xPUB484 | |
local.type.status | Published Version | |
local.contributor.affiliation | White, Lorenzo, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Schwartz, Brett, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Banwell, Martin, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Willis, Anthony, College of Physical and Mathematical Sciences, ANU | |
local.description.embargo | 2037-12-31 | |
local.bibliographicCitation.issue | 15 | |
local.bibliographicCitation.startpage | 6250 | |
local.bibliographicCitation.lastpage | 6257 | |
local.identifier.doi | 10.1021/jo201005d | |
local.identifier.absseo | 970103 - Expanding Knowledge in the Chemical Sciences | |
dc.date.updated | 2016-02-24T10:24:25Z | |
local.identifier.scopusID | 2-s2.0-79961076425 | |
local.identifier.thomsonID | 000293252600039 | |
Collections | ANU Research Publications |
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