Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone

Title
Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone
Publication Date
2016
Author(s)
Stockton, Kieran
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Royal Society of Chemistry
Place of publication
United Kingdom
DOI
10.1039/c6ob00933f
UNE publication id
une:19717
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 asymmetric 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.
Link
Citation
Organic & Biomolecular Chemistry, 14(31), p. 7520-7528
ISSN
1477-0539
1477-0520
Start page
7520
End page
7528

Files:

NameSizeformatDescriptionLink