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https://hdl.handle.net/1959.11/19527
Title: | Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone | Contributor(s): | Stockton, Kieran (author); Greatrex, Ben (author) | Publication Date: | 2016 | Open Access: | Yes | DOI: | 10.1039/c6ob00933f | Handle Link: | https://hdl.handle.net/1959.11/19527 | 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: | United Kingdom | ISSN: | 1477-0539 1477-0520 |
Fields of Research (FoR) 2008: | 030504 Organic Green Chemistry 030503 Organic Chemical Synthesis 030401 Biologically Active Molecules |
Fields of Research (FoR) 2020: | 340504 Organic green chemistry 340503 Organic chemical synthesis 340401 Biologically active molecules |
Socio-Economic Objective (SEO) 2008: | 860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics) 970103 Expanding Knowledge in the Chemical Sciences |
Socio-Economic Objective (SEO) 2020: | 240908 Organic industrial chemicals (excl. resins, rubber and plastics) 280105 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 School of Rural Medicine |
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open/SOURCE02.pdf | pre-peer review version (hidden) | 477.3 kB | Adobe PDF Download Adobe | View/Open |
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