Literature DB >> 18702502

Diazonamide support studies: stereoselective formation of the C10 chiral center in both the CDEFG and AEFG fragments.

Jinzhen Lin1, Brian S Gerstenberger, Nhu Y T Stessman, Joseph P Konopelski.   

Abstract

The synthesis of both the AEFG macrolactam and the CDEFG bis-indole/tyrosine units found in the marine natural product diazonamide A is presented. Key to the success of the synthesis is the highly stereoselective direct C-arylation of an oxindole by an aryllead(IV) reagent derived from tyrosine.

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Year:  2008        PMID： 18702502      PMCID： PMC2638117          DOI： 10.1021/ol8014336

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


  18 in total

1.  The second total synthesis of diazonamide A.

Authors:  K C Nicolaou; Paraselli Bheema Rao; Junliang Hao; Mali Venkat Reddy; Gerasimos Rassias; Xianhai Huang; David Y-K Chen; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-17       Impact factor: 15.336

2.  Total Synthesis of Nominal Diazonamides-Part 2: On the True Structure and Origin of Natural Isolates Funding provided by the NIH (RO1-GM60591), the NSF (CAREER 9984282), the Howard Hughes Medical Institute (junior faculty support), the Robert A. Welch Foundation, and the Advanced Research Program of the Texas Higher Education Coordinating Board. We are grateful to Professor Michael Roth for his time, insight, and advice.

Authors:  Jing Li; Anthony W. G. Burgett; Lothar Esser; Carlos Amezcua; Patrick G. Harran
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

3.  A concise and flexible total synthesis of (-)-diazonamide A.

Authors:  Anthony W G Burgett; Qingyi Li; Qi Wei; Patrick G Harran
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-20       Impact factor: 15.336

4.  Chemistry and biology of diazonamide A: first total synthesis and confirmation of the true structure.

Authors:  K C Nicolaou; David Y-K Chen; Xianhai Huang; Taotao Ling; Marco Bella; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

5.  Total Synthesis of Nominal Diazonamides-Part 1: Convergent Preparation of the Structure Proposed for (-)-Diazonamide A Funding provided by the NIH (RO1-GM60591), the NSF (CAREER 9984282), the Howard Hughes Medical Institute (junior faculty support), the Robert A. Welch Foundation, and the Advanced Research Program of the Texas Higher Education Coordinating Board.

Authors:  Jing Li; Susan Jeong; Lothar Esser; Patrick G. Harran
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

6.  Complete N-1 regiocontrol in the formation of N-arylimidazoles. Synthesis of the active site His-Tyr side chain coupled dipeptide of cytochrome c oxidase.

Authors:  G I Elliott; J P Konopelski
Journal:  Org Lett       Date:  2000-10-05       Impact factor: 6.005

7.  Diazonamide toxins reveal an unexpected function for ornithine delta-amino transferase in mitotic cell division.

Authors:  Gelin Wang; Libin Shang; Anthony W G Burgett; Patrick G Harran; Xiaodong Wang
Journal:  Proc Natl Acad Sci U S A       Date:  2007-02-07       Impact factor: 11.205

8.  Diazonamide A and a synthetic structural analog: disruptive effects on mitosis and cellular microtubules and analysis of their interactions with tubulin.

Authors:  Zobeida Cruz-Monserrate; Hélène C Vervoort; Ruoli Bai; David J Newman; Stephen B Howell; Gerrit Los; Jeffrey T Mullaney; Michael D Williams; George R Pettit; William Fenical; Ernest Hamel
Journal:  Mol Pharmacol       Date:  2003-06       Impact factor: 4.436

9.  Dolastatin 15 binds in the vinca domain of tubulin as demonstrated by Hummel-Dreyer chromatography.

Authors:  Zobeida Cruz-Monserrate; Jeffrey T Mullaney; Patrick G Harran; George R Pettit; Ernest Hamel
Journal:  Eur J Biochem       Date:  2003-09

10.  Structural characterization of an enantiomerically pure amino acid imidazolide and direct formation of the beta-lactam nucleus from an alpha-amino acid.

Authors:  Brian S Gerstenberger; Jinzhen Lin; Yvette S Mimieux; Lauren E Brown; Allen G Oliver; Joseph P Konopelski
Journal:  Org Lett       Date:  2008-01-09       Impact factor: 6.005
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  2 in total

1.  A concise formal synthesis of diazonamide A by the stereoselective construction of the C10 quaternary center.

Authors:  Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-22       Impact factor: 15.336

2.  Insights into soluble guanylyl cyclase activation derived from improved heme-mimetics.

Authors:  Margarete von Wantoch Rekowski; Vijay Kumar; Focco van den Akker; Athanassios Giannis; Andreas Papapetropoulos; Zongmin Zhou; Johann Moschner; Antonia Marazioti; Marina Bantzi; Georgios A Spyroulias
Journal:  J Med Chem       Date:  2013-10-24       Impact factor: 7.446
  2 in total

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