Literature DB >> 19050739

Effective Procedure for Selective Ammonolysis of Monosubstituted Oxiranes: Application to E7389 Synthesis.

Yosuke Kaburagi1, Yoshito Kishi.   

Abstract

A highly effective procedure is reported to synthesize 1,2-aminoalcohols by regio- and chemo-selective ammonolysis of monosubstituted epoxides. Additive- and concentration-effects were studied, revealing that: (1) methanesulfonic acid is most effective among the additives tested and (2) formation of bis-adducts is practically eliminated at [C] </= 40 mM. The optimum condition thus identified was successfully applied to the final step of the synthesis of potent anti-tumor compound E7389.

Entities:  

Year:  2007        PMID： 19050739      PMCID： PMC2180417          DOI： 10.1016/j.tetlet.2007.10.116

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


  15 in total

1.  Enzyme fingerprints of activity, and stereo- and enantioselectivity from fluorogenic and chromogenic substrate arrays.

Authors:  Denis Wahler; Fabrizio Badalassi; Paolo Crotti; Jean-Louis Reymond
Journal:  Chemistry       Date:  2002-07-15       Impact factor: 5.236

2.  A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

Authors:  Kosuke Namba; Hyuk-Sang Jun; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2004-06-30       Impact factor: 15.419

3.  A wrench-shaped synthetic molecule that modulates a transcription factor-coactivator interaction.

Authors:  Hiroki Shimogawa; Youngjoo Kwon; Qian Mao; Yoshinori Kawazoe; Yongmun Choi; Shinichi Asada; Hideo Kigoshi; Motonari Uesugi
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419

4.  Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis.

Authors:  M Tokunaga; J F Larrow; F Kakiuchi; E N Jacobsen
Journal:  Science       Date:  1997-08-15       Impact factor: 47.728

5.  Structure-based design of potent and selective cell-permeable inhibitors of human beta-secretase (BACE-1).

Authors:  Shawn J Stachel; Craig A Coburn; Thomas G Steele; Kristen G Jones; Elizabeth F Loutzenhiser; Alison R Gregro; Hemaka A Rajapakse; Ming-Tain Lai; Ming-Chih Crouthamel; Min Xu; Katherine Tugusheva; Janet E Lineberger; Beth L Pietrak; Amy S Espeseth; Xiao-Ping Shi; Elizabeth Chen-Dodson; M Katharine Holloway; Sanjeev Munshi; Adam J Simon; Lawrence Kuo; Joseph P Vacca
Journal:  J Med Chem       Date:  2004-12-16       Impact factor: 7.446

6.  Catalytic Ni/Cr-mediated macrocyclization without use of high-dilution techniques.

Authors:  Kosuke Namba; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

7.  Advances in homogeneous and heterogeneous catalytic asymmetric epoxidation.

Authors:  Q-H Xia; H-Q Ge; C-P Ye; Z-M Liu; K-X Su
Journal:  Chem Rev       Date:  2005-05       Impact factor: 60.622

8.  Catalytic regioselective sulfonylation of alpha-chelatable alcohols: scope and mechanistic insight.

Authors:  Michael J Martinelli; Rajappa Vaidyanathan; Joseph M Pawlak; Naresh K Nayyar; Ulhas P Dhokte; Christopher W Doecke; Lisa M H Zollars; Eric D Moher; Vien Van Khau; Berta Kosmrlj
Journal:  J Am Chem Soc       Date:  2002-04-10       Impact factor: 15.419

9.  The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth.

Authors:  Mary Ann Jordan; Kathryn Kamath; Tapas Manna; Tatiana Okouneva; Herbert P Miller; Celia Davis; Bruce A Littlefield; Leslie Wilson
Journal:  Mol Cancer Ther       Date:  2005-07       Impact factor: 6.261

10.  Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.

Authors:  Yosuke Kaburagi; Yoshito Kishi
Journal:  Org Lett       Date:  2007-02-15       Impact factor: 6.005
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  2 in total

1.  Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.

Authors:  Hai-Yang Wang; Kun Huang; Melvin De Jesús; Sandraliz Espinosa; Luis E Piñero-Santiago; Charles L Barnes; Margarita Ortiz-Marciales
Journal:  Tetrahedron Asymmetry       Date:  2016-02-15

Review 2.  Capturing Biological Activity in Natural Product Fragments by Chemical Synthesis.

Authors:  Erika A Crane; Karl Gademann
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336
  2 in total

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