Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

Kieran P. Stockton; Ben W. Greatrex

doi:10.1039/c6ob00933f

Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

Kieran P. Stockton, Ben W. Greatrex

Research output: Contribution to journal › Article › Research › peer-review

14 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 GABA_c 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 language	English
Pages (from-to)	7520-7528
Number of pages	9
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	31
DOIs	https://doi.org/10.1039/c6ob00933f
Publication status	Published - 21 Aug 2016
Externally published	Yes

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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.",

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AU - Greatrex, Ben W.

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PY - 2016/8/21

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N2 - 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.

AB - 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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JO - Organic & Biomolecular Chemistry

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ER -

Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

Abstract

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