Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.

Issue 31, 2016
Previous Article Next Article

Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone

Author affiliations


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

Back to tab navigation

Supplementary files

Article information

18 Jun 2016
08 Jul 2016
First published
12 Jul 2016

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

Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone

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

Social activity

Search articles by author