Approaches to the Synthesis of the Galbulimima Alkaloid Himandrine
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O'Connor, Patrick; Del Signore, Giuseppe; McLachlan, Matthew; Willis, Anthony; Mander, Lewis
Description
The hexacyclic skeleton of himandrine (2), which is present in 15 of the more complex alkaloids obtained from the bark of the tropical rain forest tree Galbulimima belgraveana has been prepared by means of a 19-step synthesis beginning with the known [3.2.1]-benzobicyclooctene intermediate 9. An alternative approach is also described, thus far culminating in 34. Key transformations include DielsAlder cycloadditions, ring contractions, a Curtius rearrangement, a Birch reduction, an...[Show more]
dc.contributor.author | O'Connor, Patrick | |
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dc.contributor.author | Del Signore, Giuseppe | |
dc.contributor.author | McLachlan, Matthew | |
dc.contributor.author | Willis, Anthony | |
dc.contributor.author | Mander, Lewis | |
dc.date.accessioned | 2015-12-10T22:40:58Z | |
dc.identifier.issn | 0004-9425 | |
dc.identifier.uri | http://hdl.handle.net/1885/57685 | |
dc.description.abstract | The hexacyclic skeleton of himandrine (2), which is present in 15 of the more complex alkaloids obtained from the bark of the tropical rain forest tree Galbulimima belgraveana has been prepared by means of a 19-step synthesis beginning with the known [3.2.1]-benzobicyclooctene intermediate 9. An alternative approach is also described, thus far culminating in 34. Key transformations include DielsAlder cycloadditions, ring contractions, a Curtius rearrangement, a Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination. | |
dc.publisher | CSIRO Publishing | |
dc.source | Australian Journal of Chemistry | |
dc.subject | Keywords: Alternative approach; Birch reduction; Diels-Alder cycloadditions; Ring contraction; Tropical rain forest; Amines; Metabolites; Olefins; Palladium; Chemical compounds | |
dc.title | Approaches to the Synthesis of the Galbulimima Alkaloid Himandrine | |
dc.type | Journal article | |
local.description.notes | Imported from ARIES | |
local.identifier.citationvolume | 63 | |
dc.date.issued | 2010 | |
local.identifier.absfor | 030503 - Organic Chemical Synthesis | |
local.identifier.ariespublication | u4005981xPUB411 | |
local.type.status | Published Version | |
local.contributor.affiliation | O'Connor, Patrick, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Del Signore, Giuseppe, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | McLachlan, Matthew, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Willis, Anthony, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Mander, Lewis, College of Physical and Mathematical Sciences, ANU | |
local.description.embargo | 2037-12-31 | |
local.bibliographicCitation.issue | 10 | |
local.bibliographicCitation.startpage | 1477 | |
local.bibliographicCitation.lastpage | 1491 | |
local.identifier.doi | 10.1071/CH10252 | |
local.identifier.absseo | 970103 - Expanding Knowledge in the Chemical Sciences | |
dc.date.updated | 2016-02-24T10:23:38Z | |
local.identifier.scopusID | 2-s2.0-77957722848 | |
local.identifier.thomsonID | 000282433800011 | |
Collections | ANU Research Publications |
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