Enantio- and Diastereoselective Synthesis of (R,R)-β-Methoxytyrosine

Enantio- and Diastereoselective Synthesis of (R,R)-β-Methoxytyrosine

The nonproteinogenic amino acid (2R,3R)-β-methoxytyrosine, a constituent of several cyclic depsipeptide natural products, was synthesized in protected form (8) from a readily available cinnamate ester in four steps and 62% overall yield with a greater than 28:1 er and 19:1 dr. This method provides a...

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Veröffentlicht in:Organic letters 2007-08, Vol.9 (18), p.3511-3513
Hauptverfasser: Cranfill, David C, Lipton, Mark A
Format: Artikel
Sprache:eng
Schlagworte:
Cinnamates - chemistry
Depsipeptides - chemistry
Esters - chemistry
Molecular Structure
Stereoisomerism
Tyrosine - analogs & derivatives
Tyrosine - chemical synthesis
Tyrosine - chemistry
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Zusammenfassung:The nonproteinogenic amino acid (2R,3R)-β-methoxytyrosine, a constituent of several cyclic depsipeptide natural products, was synthesized in protected form (8) from a readily available cinnamate ester in four steps and 62% overall yield with a greater than 28:1 er and 19:1 dr. This method provides a highly efficient, enantio- and diastereoselective synthesis of an important amino acid.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol071350u