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Enantio- and diastereoselective synthesis of (R,R)-beta-methoxytyrosine.

ABSTRACT: The nonproteinogenic amino acid (2R,3R)-beta-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.

SUBMITTER: Cranfill DC

PROVIDER: S-EPMC2688733 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature

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Enantio- and diastereoselective synthesis of (R,R)-beta-methoxytyrosine.

Cranfill David C DC Lipton Mark A MA

Organic letters 20070803 18

The nonproteinogenic amino acid (2R,3R)-beta-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. ...[more]

PMID: 17676746

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