Synthesis of non-proteinogenic amino acids using Michael addition to unsaturated orthopyroglutamate derivative

Stereoselective synthesis of non-proteinogenic amino acids via Michael addition to 3,4-didehydropyroglutamate derivative in which the carboxyl function is protected as a 2,7,8-trioxabicyclo[3.2.1]octane (ABO ester) group is described. The obtained 3-substituted pyroglutamic ABO ester was directly co...

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Bibliographic Details
Published in:Tetrahedron 2009-01, Vol.65 (1), p.128-133
Main Authors: Oba, Makoto, Saegusa, Tsuneki, Nishiyama, Naohiro, Nishiyama, Kozaburo
Format: Article
Language:English
Subjects:
ABO ester
Amino acids
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Michael addition
Organic chemistry
Preparations and properties
Pyroglutaminol
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Summary:Stereoselective synthesis of non-proteinogenic amino acids via Michael addition to 3,4-didehydropyroglutamate derivative in which the carboxyl function is protected as a 2,7,8-trioxabicyclo[3.2.1]octane (ABO ester) group is described. The obtained 3-substituted pyroglutamic ABO ester was directly converted to 3-substituted glutamic acids such as chlorpheg by acidic hydrolysis, whereas 3-substituted proline derivatives were obtained by chemoselective reduction of the lactam carbonyl group. A formal total synthesis of baclofen, a γ-aminobutyric acid (GABA) analogue, is also described. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.10.092