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.
| Original language | English |
|---|---|
| Pages (from-to) | 7520-7528 |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 14 |
| Issue number | 31 |
| DOIs | |
| Publication status | Published - 2016 |
Keywords
- Organic Chemical Synthesis
- Biologically Active Molecules
- Organic Green Chemistry
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