Total Synthesis of the Galbulimima Alkaloid (±)-GB 13
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McLachlan, Matthew; O'Connor, Patrick; Fairweather, Kelly Ann; Willis, Anthony; Mander, Lewis
Description
The synthesis of alkaloid GB 13 (4), isolated from the North Australian rain forest tree Galbulimima belgraveana is described. Birch reductive alkylation of 2,5-dimethoxybenzoic acid by 3-methoxybenzyl bromide, followed by an acidcatalyzed cyclization was used to synthesize the [3.3.1]bicyclononane 12. Ring contraction performed on the diazoketone 19 followed by a Diels-Alder reaction generated a pentacyclic intermediate 34 with a carbon skeleton closely resembling the target alkaloid. The...[Show more]
dc.contributor.author | McLachlan, Matthew | |
---|---|---|
dc.contributor.author | O'Connor, Patrick | |
dc.contributor.author | Fairweather, Kelly Ann | |
dc.contributor.author | Willis, Anthony | |
dc.contributor.author | Mander, Lewis | |
dc.date.accessioned | 2015-12-07T22:26:58Z | |
dc.identifier.issn | 0004-9425 | |
dc.identifier.uri | http://hdl.handle.net/1885/21674 | |
dc.description.abstract | The synthesis of alkaloid GB 13 (4), isolated from the North Australian rain forest tree Galbulimima belgraveana is described. Birch reductive alkylation of 2,5-dimethoxybenzoic acid by 3-methoxybenzyl bromide, followed by an acidcatalyzed cyclization was used to synthesize the [3.3.1]bicyclononane 12. Ring contraction performed on the diazoketone 19 followed by a Diels-Alder reaction generated a pentacyclic intermediate 34 with a carbon skeleton closely resembling the target alkaloid. The surplus nitrile substituent, required for activation and regioselectivity in the Diels-Alder reaction, was removed by treatment with lithium and liquid ammonia. Birch reduction of the aromatic ring could be performed at the same time to give diene 38 and thence enone 41, which was cleaved by means of an Eschenmoser fragmentation. The piperidine ring found in the natural product was formed by reductive cyclization of bis-oxime 49 derived from the alkynyl ketone 48 and the resulting material further elaborated to GB 13. | |
dc.publisher | CSIRO Publishing | |
dc.source | Australian Journal of Chemistry | |
dc.subject | Keywords: A-carbon; Alkynyls; Aromatic rings; Birch reduction; Diazoketones; Diels-Alder reaction; Liquid ammonia; Natural products; Piperidine rings; Rain forests; Reductive alkylation; Reductive cyclization; Resulting materials; Ring contraction; Total synthesis; | |
dc.title | Total Synthesis of the Galbulimima Alkaloid (±)-GB 13 | |
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 | u4029839xPUB18 | |
local.type.status | Published Version | |
local.contributor.affiliation | McLachlan, Matthew, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | O'Connor, Patrick, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Fairweather, Kelly Ann, 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 | 5 | |
local.bibliographicCitation.startpage | 742 | |
local.bibliographicCitation.lastpage | 760 | |
local.identifier.doi | 10.1071/CH10056 | |
local.identifier.absseo | 970103 - Expanding Knowledge in the Chemical Sciences | |
dc.date.updated | 2016-02-24T10:29:49Z | |
local.identifier.scopusID | 2-s2.0-77952991870 | |
local.identifier.thomsonID | 000277891900003 | |
Collections | ANU Research Publications |
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