Enantioselective Synthesis of the Excitatory Amino Acid (1S,3R)-1-Aminocyclopentane-1,3-dicarboxylic Acid

An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent cataly...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-11, Vol.67 (22), p.7613-7617
Main Authors: Bradley, Daniel M, Mapitse, Renameditswe, Thomson, Nicholas M, Hayes, Christopher J
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Cycloleucine - analogs & derivatives
Cycloleucine - chemical synthesis
Cycloleucine - chemistry
Exact sciences and technology
Excitatory Amino Acids - chemical synthesis
Excitatory Amino Acids - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:An enantioselective synthesis of the α,α-dialkyl-α-amino acid (1S,3R)-ACPD has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The ketone cyclization precursor was synthesized from Garner's aldehyde in high yield via a Wittig homologation and subsequent catalytic hydrogenation. Treatment of the ketone with 1.2 equiv of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the corresponding cyclopentene-containing CH-insertion product in 62−69% yield in high enantiomeric excess. Subsequent functional group manipulation allowed the synthesis of the amino acid (1S,3R)-ACPD to be completed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo025892v