Literature DB >> 19644565

Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.

Minoru Ikoma1, Masato Oikawa, Martin B Gill, Geoffrey T Swanson, Ryuichi Sakai, Keiko Shimamoto, Makoto Sasaki.   

Abstract

A highly regioselective domino metathesis reaction of 7-oxanorbornene was developed that employed an intramolecular association of an amide carbonyl group to a ruthenium metal centre. By using this reaction, twelve glutamate analogues inspired by dysiherbaine were efficiently synthesized over 12-14 steps; one of the analogues exhibited bioactivity consistent with central nervous system depression.

Entities:  

Year:  2008        PMID： 19644565      PMCID： PMC2717718          DOI： 10.1002/ejoc.200800704

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  20 in total

1.  Recent developments in olefin cross-metathesis.

Authors:  Stephen J Connon; Siegfried Blechert
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-29       Impact factor: 15.336

2.  Kinetically controlled cross-metathesis reactions with high E-olefin selectivities.

Authors:  F C Engelhardt; M J Schmitt; R E Taylor
Journal:  Org Lett       Date:  2001-07-12       Impact factor: 6.005

3.  Metathesis reactions in total synthesis.

Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

4.  Ring-opening/ring-closing metathesis (RORCM) reactions of 7-Azanorbornene derivatives. An entry into perhydroindolines.

Authors:  Zhuqing Liu; Jon D Rainier
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

Review 5.  The remarkable metal-catalysed olefin metathesis reaction.

Authors:  Amir H Hoveyda; Adil R Zhugralin
Journal:  Nature       Date:  2007-11-08       Impact factor: 49.962

6.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors:  M Scholl; S Ding; C W Lee; R H Grubbs
Journal:  Org Lett       Date:  1999-09-23       Impact factor: 6.005

7.  Total synthesis of salinosporamide A.

Authors:  Atsushi Endo; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

8.  Divergent pharmacological activity of novel marine-derived excitatory amino acids on glutamate receptors.

Authors:  James M Sanders; Koichi Ito; Luca Settimo; Olli T Pentikäinen; Muneo Shoji; Makoto Sasaki; Mark S Johnson; Ryuichi Sakai; Geoffrey T Swanson
Journal:  J Pharmacol Exp Ther       Date:  2005-05-24       Impact factor: 4.030

9.  Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton.

Authors:  Ken-ichi Takao; Hiroyuki Yasui; Shun Yamamoto; Daisuke Sasaki; Soujiro Kawasaki; Gohshi Watanabe; Kin-ichi Tadano
Journal:  J Org Chem       Date:  2004-12-10       Impact factor: 4.354

10.  Highly regioselective ring-opening/cross-metathesis reactions of 2-sulfonylnorbornene derivatives.

Authors:  G Mahika Weeresakare; Zhuqing Liu; Jon D Rainier
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005
View more
  10 in total

1.  A series of structurally novel heterotricyclic alpha-amino-3-hydroxyl-5-methyl-4-isoxazole-propionate receptor-selective antagonists.

Authors:  M B Gill; S Frausto; M Ikoma; M Sasaki; M Oikawa; R Sakai; G T Swanson
Journal:  Br J Pharmacol       Date:  2010-07       Impact factor: 8.739

2.  Improved synthesis and in vitro/in vivo activities of natural product-inspired, artificial glutamate analogs.

Authors:  Masato Oikawa; Minoru Ikoma; Makoto Sasaki; Martin B Gill; Geoffrey T Swanson; Keiko Shimamoto; Ryuichi Sakai
Journal:  Bioorg Med Chem       Date:  2010-04-21       Impact factor: 3.641

3.  Studies on an (S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonist IKM-159: asymmetric synthesis, neuroactivity, and structural characterization.

Authors:  Lina Juknaitė; Yutaro Sugamata; Kazuya Tokiwa; Yuichi Ishikawa; Satoshi Takamizawa; Andrew Eng; Ryuichi Sakai; Darryl S Pickering; Karla Frydenvang; Geoffrey T Swanson; Jette S Kastrup; Masato Oikawa
Journal:  J Med Chem       Date:  2013-03-13       Impact factor: 7.446

4.  Regioselective Domino Metathesis of Unsymmetrical 7-Oxanorbornenes with Electron-Rich Vinyl Acetate toward Biologically Active Glutamate Analogues.

Authors:  Masato Oikawa; Minoru Ikoma; Makoto Sasaki; Martin B Gill; Geoffrey T Swanson; Keiko Shimamoto; Ryuichi Sakai
Journal:  European J Org Chem       Date:  2009-11-01

5.  Enantioselective synthesis of 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans via [4 + 2] cycloaddition and ring-opening cross-metathesis.

Authors:  Noah M Benjamin; Stephen F Martin
Journal:  Org Lett       Date:  2011-01-06       Impact factor: 6.005

6.  Metathesis Cascade Strategies (ROM-RCM-CM): A DOS approach to Skeletally Diverse Sultams.

Authors:  Kyu Ok Jeon; Dinesh Rayabarapu; Alan Rolfe; Kelly Volp; Iman Omar; Paul R Hanson
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

Review 7.  Recent progress in neuroactive marine natural products.

Authors:  Ryuichi Sakai; Geoffrey T Swanson
Journal:  Nat Prod Rep       Date:  2014-01-17       Impact factor: 13.423

8.  Menthyl esterification allows chiral resolution for the synthesis of artificial glutamate analogs.

Authors:  Kenji Morokuma; Shuntaro Tsukamoto; Kyosuke Mori; Kei Miyako; Ryuichi Sakai; Raku Irie; Masato Oikawa
Journal:  Beilstein J Org Chem       Date:  2021-02-24       Impact factor: 2.883

9.  Oxa-Michael-based divergent synthesis of artificial glutamate analogs.

Authors:  Shuntaro Tsukamoto; Oriel Hlokoane; Kei Miyako; Raku Irie; Ryuichi Sakai; Masato Oikawa
Journal:  RSC Adv       Date:  2022-08-10       Impact factor: 4.036

Review 10.  Recent applications of ring-rearrangement metathesis in organic synthesis.

Authors:  Sambasivarao Kotha; Milind Meshram; Priti Khedkar; Shaibal Banerjee; Deepak Deodhar
Journal:  Beilstein J Org Chem       Date:  2015-10-07       Impact factor: 2.883
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.