Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

Kieran P. Stockton, Ben W. Greatrex

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17 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7520-7528
Number of pages9
JournalOrganic & Biomolecular Chemistry
Volume14
Issue number31
DOIs
Publication statusPublished - 21 Aug 2016
Externally publishedYes

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