Jump to main content
Jump to site search

Issue 31, 2016
Previous Article Next Article

Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Jun 2016, accepted on 08 Jul 2016 and first published on 12 Jul 2016


Article type: Paper
DOI: 10.1039/C6OB00933F
Citation: Org. Biomol. Chem., 2016,14, 7520-7528
  •   Request permissions

    Synthesis of enantiopure cyclopropyl esters from (−)-levoglucosenone

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

Search articles by author

Spotlight

Advertisements