Synthesis of enantiopure cyclopropyl esters from (?)-levoglucosenone?
Organic & Biomolecular Chemistry Pub Date: 2016-07-12 DOI: 10.1039/C6OB00933F
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 enantiospecific 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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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