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Issue 31, 2016
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Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone

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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 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.

Graphical abstract: Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone

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Supplementary files

Article information


Submitted
18 Jun 2016
Accepted
08 Jul 2016
First published
12 Jul 2016

Org. Biomol. Chem., 2016,14, 7520-7528
Article type
Paper

Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone

K. P. Stockton and B. W. Greatrex, Org. Biomol. Chem., 2016, 14, 7520
DOI: 10.1039/C6OB00933F

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