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Literature DB >> 11671510

Synthesis of (9R,12S)- and (9S,12S)-Cycloisodityrosine and Their N-Methyl Derivatives.

Dale L. Boger¹, Jiacheng Zhou, Robert M. Borzilleri, Seiji Nukui, Steven L. Castle.

Abstract

Full details of the synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives are detailed based on an intramolecular nucleophilic aromatic substitution reaction for formation of the key biaryl ether with 14-membered ring macrocyclization. Their comparison with prior samples and the documentation of a facile C9 epimerization within the natural 9S series are described.

Entities: Chemical

Year: 1997 PMID： 11671510 DOI： 10.1021/jo961346o

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

5 in total

1. 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

2. Total synthesis of [Ψ[C(═S)NH]Tpg4]vancomycin aglycon, [Ψ[C(═NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

Authors: Jian Xie; Akinori Okano; Joshua G Pierce; Robert C James; Simon Stamm; Christine M Crane; Dale L Boger
Journal: J Am Chem Soc Date: 2012-01-06 Impact factor: 15.419

Synthesis of (9R,12S)- and (9S,12S)-Cycloisodityrosine and Their N-Methyl Derivatives.

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

2. Total synthesis of [Ψ[C(═S)NH]Tpg4]vancomycin aglycon, [Ψ[C(═NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

3. One-pot high-throughput synthesis of beta-turn cyclic peptidomimetics via "volatilizable" supports.

Review 4. Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues.

Review 5. Design and synthesis of analogues of RA-VII-an antitumor bicyclic hexapeptide from Rubiae radix.