Literature DB >> 17676746

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

David C Cranfill1, Mark A Lipton.   

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.

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Year:  2007        PMID： 17676746      PMCID： PMC2688733          DOI： 10.1021/ol071350u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Dynamic kinetic resolution catalyzed by Ir axially chiral phosphine catalyst: asymmetric synthesis of anti aromatic beta-hydroxy-alpha-amino acid esters.

Authors:  Kazuishi Makino; Yasuhiro Hiroki; Yasumasa Hamada
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

2.  Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A.

Authors:  Angela Zampella; Rosa D'Orsi; Valentina Sepe; Agostino Casapullo; Maria Chiara Monti; Maria Valeria D'Auria
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

3.  Complete stereochemistry of neamphamide A and absolute configuration of the beta-methoxytyrosine residue in papuamide B.

Authors:  Naoya Oku; Ravi Krishnamoorthy; Alan G Benson; Robert L Ferguson; Mark A Lipton; Lawrence R Phillips; Kirk R Gustafson; James B McMahon
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

4.  Versatile and stereoselective syntheses of orthogonally protected beta-methylcysteine and beta-methyllanthionine.

Authors:  Radha S Narayan; Michael S Vannieuwenhze
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

5.  Stereoselective synthesis of four stereoisomers of beta-methoxytyrosine, a component of callipeltin A.

Authors:  Darren B Hansen; Xiaobo Wan; Patrick J Carroll; Madeleine M Joullié
Journal:  J Org Chem       Date:  2005-04-15       Impact factor: 4.354

6.  Diastereoselective synthesis of all stereoisomers of beta-methoxytyrosine, a component of papuamides.

Authors:  Naoki Okamoto; Osamu Hara; Kazuishi Makino; Yasumasa Hamada
Journal:  J Org Chem       Date:  2002-12-27       Impact factor: 4.354

7.  A novel and convenient chemoselective deprotection method for both silyl and acetyl groups on acidic hydroxyl groups such as phenol and carboxylic acid by using a nitrogen organic base, 1,1,3,3-tetramethylguanidine.

Authors:  Kin-ichi Oyama; Tadao Kondo
Journal:  Org Lett       Date:  2003-01-23       Impact factor: 6.005
  7 in total
  3 in total

1.  Chemo- and Enantioselective Intramolecular Silver-Catalyzed Aziridinations.

Authors:  Minsoo Ju; Cale D Weatherly; Ilia A Guzei; Jennifer M Schomaker
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

2.  Ligand-Enabled γ-C(sp(3))-H Olefination of Amines: En Route to Pyrrolidines.

Authors:  Heng Jiang; Jian He; Tao Liu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-02-04       Impact factor: 15.419

3.  Enantioselective ortho-C-H cross-coupling of diarylmethylamines with organoborons.

Authors:  Brian N Laforteza; Kelvin S L Chan; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-04       Impact factor: 15.336
  3 in total

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