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Title: Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone
Contributor(s): Stockton, Kieran (author); Greatrex, Ben  (author)orcid 
Publication Date: 2016
Open Access: Yes
DOI: 10.1039/c6ob00933f
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Abstract: The biorenewable chiral synthon (-)-levoglucosenone has been converted to enantiopure cyclopropyl esters using the base-promoted carbocyclisation of 4,5-epoxyvalerates. This protocol was applied to the asymmetric synthesis of the GABAc receptor agonist (1R,2R)-trans-2-aminomethylcyclopropanecarboxylic acid ((-)-TAMP) and its enantiomer. The process was also extended to generate 1,1,2- and 1,2,3-trisubstituted cyclopropanes resulting in a formal synthesis of the selective glutamate receptor antagonist PCCG-4.
Publication Type: Journal Article
Source of Publication: Organic & Biomolecular Chemistry, 14(31), p. 7520-7528
Publisher: Royal Society of Chemistry
Place of Publication: Cambridge, United Kingdom
ISSN: 1477-0520
Field of Research (FoR) 2008: 030504 Organic Green Chemistry
030503 Organic Chemical Synthesis
030401 Biologically Active Molecules
Socio-Economic Objective (SEO) 2008: 860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)
970103 Expanding Knowledge in the Chemical Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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Appears in Collections:Journal Article
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