Literature DB >> 19593390

An Operationally Simple and Efficient Synthesis of Orthogonally Protected L-threo-beta-Hydroxyasparagine.

Aikomari Guzmán-Martinez1, Michael S Vannieuwenhze.   

Abstract

A synthesis of orthogonally protected L-threo-beta-hydroxyasparagine from L-aspartic acid is reported. Iodocyclization of 3-benzoylaminoaspartic acid provided an intermediate oxazoline dicarboxylate that was efficiently hydrolyzed to L-threo-beta-hydroxyaspartic acid. The synthetic route for conversion of the free beta-hydroxy-alpha-amino acid into the target compound is highly efficient and amenable to preparation various orthogonally protected asparagine derivatives, on a multiple gram scale.

Entities:  

Year:  2007        PMID： 19593390      PMCID： PMC2707822          DOI： 10.1055/s-2007-982544

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  8 in total

1.  Asymmetric synthesis of orthogonally protected L-threo-beta-hydroxyasparagine.

Authors:  D L Boger; R J Lee; P Y Bounaud; P Meier
Journal:  J Org Chem       Date:  2000-10-06       Impact factor: 4.354

2.  A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure.

Authors:  Travis Dudding; Ahmed M Hafez; Andrew E Taggi; Ty R Wagerle; Thomas Lectka
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

3.  Katanosin B and plusbacin A(3), inhibitors of peptidoglycan synthesis in methicillin-resistant Staphylococcus aureus.

Authors:  H Maki; K Miura; Y Yamano
Journal:  Antimicrob Agents Chemother       Date:  2001-06       Impact factor: 5.191

4.  Isolation and characterization of katanosins A and B.

Authors:  J Shoji; H Hinoo; K Matsumoto; T Hattori; T Yoshida; S Matsuura; E Kondo
Journal:  J Antibiot (Tokyo)       Date:  1988-06       Impact factor: 2.649

5.  A multistage, one-pot procedure mediated by a single catalyst: a new approach to the catalytic asymmetric synthesis of beta-amino acids.

Authors:  Ahmed M Hafez; Travis Dudding; Ty R Wagerle; Meha H Shah; Andrew E Taggi; Thomas Lectka
Journal:  J Org Chem       Date:  2003-07-25       Impact factor: 4.354

6.  Threo- and erythro-beta-hydroxyl-l-asparagines.

Authors:  A Singerman; Y Liwschitz
Journal:  Tetrahedron Lett       Date:  1968-09       Impact factor: 2.415

7.  N-carboxy-anhydrides derived from threo- and erythro-beta-hydroxy-aspartic acids and poly-beta-methyl hydrogen threo-beta-methoxyl-DL-aspartate.

Authors:  Y Liwschitz; A Singerman
Journal:  J Chem Soc Perkin 1       Date:  1967

8.  The structures of katanosins A and B.

Authors:  T Kato; H Hinoo; Y Terui; J Kikuchi; J Shoji
Journal:  J Antibiot (Tokyo)       Date:  1988-06       Impact factor: 2.649
  8 in total
  3 in total

1.  Solid-phase synthesis of lysobactin (katanosin B): insights into structure and function.

Authors:  Edward A Hall; Erkin Kuru; Michael S VanNieuwenhze
Journal:  Org Lett       Date:  2012-05-21       Impact factor: 6.005

2.  Divergent synthesis of biologically active L-threo-β-hydroxyaspartates from common trans-oxazolidine dicarboxylate.

Authors:  Yoonjae Lee; Youngran Seo; Boram Lee; Hyuenyoung Kwon; Kyungsu Chung; Young Gyu Kim
Journal:  Amino Acids       Date:  2022-08-13       Impact factor: 3.789

3.  Gatorbulin-1, a distinct cyclodepsipeptide chemotype, targets a seventh tubulin pharmacological site.

Authors:  Susan Matthew; Qi-Yin Chen; Ranjala Ratnayake; Charles S Fermaintt; Daniel Lucena-Agell; Francesca Bonato; Andrea E Prota; Seok Ting Lim; Xiaomeng Wang; J Fernando Díaz; April L Risinger; Valerie J Paul; Maria Ángela Oliva; Hendrik Luesch
Journal:  Proc Natl Acad Sci U S A       Date:  2021-03-02       Impact factor: 11.205
  3 in total

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