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

21 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

Access to Document

10.1039/c6ob00933f

Cite this

@article{1f05e32af165481fb916ac6d56f7d362,

title = "Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone",

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.",

author = "Stockton, \{Kieran P.\} and Greatrex, \{Ben W.\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

month = aug,

day = "21",

doi = "10.1039/c6ob00933f",

language = "English",

volume = "14",

pages = "7520--7528",

journal = "Organic \& Biomolecular Chemistry",

issn = "1477-0520",

publisher = "The Royal Society of Chemistry",

number = "31",

}

TY - JOUR

T1 - Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

AU - Stockton, Kieran P.

AU - Greatrex, Ben W.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2016.

PY - 2016/8/21

Y1 - 2016/8/21

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.

UR - https://www.scopus.com/pages/publications/84981283751

U2 - 10.1039/c6ob00933f

DO - 10.1039/c6ob00933f

M3 - Article

C2 - 27424764

AN - SCOPUS:84981283751

SN - 1477-0520

VL - 14

SP - 7520

EP - 7528

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 31

ER -

Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

Abstract

Access to Document

Other files and links

Cite this