Literature DB >> 21516235

Total synthesis of LL-Z1640-2 utilizing a late-stage intramolecular Nozaki-Hiyama-Kishi reaction.

Christopher A Leclair1, Matthew B Boxer, Craig J Thomas, David J Maloney.   

Abstract

A total synthesis of LL-Z1640-2 (2), a potent and selective kinase inhibitor, has been completed. The key step of the convergent synthesis utilized a late-stage intramolecular Nozaki-Hiyama-Kishi (NHK) reaction to close the macrocycle at the C6'-C7' bond.

Entities:  

Year:  2010        PMID： 21516235      PMCID： PMC3079232          DOI： 10.1016/j.tetlet.2010.10.092

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  20 in total

1.  Modular synthesis of radicicol A and related resorcylic acid lactones, potent kinase inhibitors.

Authors:  Pierre-Yves Dakas; Sofia Barluenga; Frank Totzke; Ute Zirrgiebel; Nicolas Winssinger
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

2.  Semisynthesis and cytotoxicity of hypothemycin analogues.

Authors:  Brian R Hearn; Kurt Sundermann; Jonah Cannoy; Daniel V Santi
Journal:  ChemMedChem       Date:  2007-11       Impact factor: 3.466

Review 3.  Chemistry and biology of resorcylic acid lactones.

Authors:  Nicolas Winssinger; Sofia Barluenga
Journal:  Chem Commun (Camb)       Date:  2006-09-25       Impact factor: 6.222

4.  A radicicol-related macrocyclic nonaketide compound, antibiotic LL-Z1640-2, inhibits the JNK/p38 pathways in signal-specific manner.

Authors:  K Takehana; S Sato; T Kobayasi; T Maeda
Journal:  Biochem Biophys Res Commun       Date:  1999-04-02       Impact factor: 3.575

5.  Molecular editing of kinase-targeting resorcylic acid lactones (RAL): Fluoroenone RAL.

Authors:  Rajamalleswaramma Jogireddy; Sofia Barluenga; Nicolas Winssinger
Journal:  ChemMedChem       Date:  2010-05-03       Impact factor: 3.466

6.  Resorcylic acid lactones: naturally occurring potent and selective inhibitors of MEK.

Authors:  A Zhao; S H Lee; M Mojena; R G Jenkins; D R Patrick; H E Huber; M A Goetz; O D Hensens; D L Zink; D Vilella; A W Dombrowski; R B Lingham; L Huang
Journal:  J Antibiot (Tokyo)       Date:  1999-12       Impact factor: 2.649

7.  Total synthesis of aigialomycin D.

Authors:  Xudong Geng; Samuel J Danishefsky
Journal:  Org Lett       Date:  2004-02-05       Impact factor: 6.005

8.  A formal synthesis of the callipeltoside aglycone.

Authors:  James A Marshall; Patrick M Eidam
Journal:  Org Lett       Date:  2007-12-05       Impact factor: 6.005

9.  Inhibition of endotoxin-induced TNF-alpha production in macrophages by 5Z-7-oxo-zeaenol and other fungal resorcylic acid lactones.

Authors:  P Rawlins; T Mander; R Sadeghi; S Hill; G Gammon; B Foxwell; S Wrigley; M Moore
Journal:  Int J Immunopharmacol       Date:  1999-12

10.  A resorcylic acid lactone, 5Z-7-oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase.

Authors:  Jun Ninomiya-Tsuji; Taisuke Kajino; Koichiro Ono; Toshihiko Ohtomo; Masahiko Matsumoto; Masashi Shiina; Masahiko Mihara; Masayuki Tsuchiya; Kunihiro Matsumoto
Journal:  J Biol Chem       Date:  2003-03-06       Impact factor: 5.486
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  1 in total

Review 1.  Natural and Synthetic Lactones Possessing Antitumor Activities.

Authors:  Younghoon Kim; Sandip Sengupta; Taebo Sim
Journal:  Int J Mol Sci       Date:  2021-01-21       Impact factor: 6.208
  1 in total

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