Literature DB >> 22954141

Enantioselective total synthesis of pladienolide B: a potent spliceosome inhibitor.

Arun K Ghosh1, David D Anderson.   

Abstract

An enantioselective and convergent total synthesis of pladienolide B (1) is described. Pladienolide B binds to the SF3b complex of a spliceosome and inhibits mRNA splicing activity. The synthesis features an epoxide opening reaction, an asymmetric reduction of a β-keto ester, and a cross metathesis strategy for the side chain synthesis.

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Year:  2012        PMID： 22954141      PMCID： PMC3482479          DOI： 10.1021/ol301886g

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


  17 in total

1.  Some allylic substituent effects in ring-closing metathesis reactions: allylic alcohol activation.

Authors:  T R Hoye; H Zhao
Journal:  Org Lett       Date:  1999-10-07       Impact factor: 6.005

2.  On the selective deprotection of trityl ethers.

Authors:  G B Jones; G Hynd; J M Wright; A Sharma
Journal:  J Org Chem       Date:  2000-01-14       Impact factor: 4.354

3.  Total synthesis of the potent antitumor macrolides pladienolide B and D.

Authors:  Regina M Kanada; Daisuke Itoh; Mitsuo Nagai; Jun Niijima; Naoki Asai; Yoshiharu Mizui; Shinya Abe; Yoshihiko Kotake
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Design, synthesis and initial biological evaluation of a novel pladienolide analog scaffold.

Authors:  Mahesh Kumar Gundluru; Alan Pourpak; Xiaoli Cui; Stephan W Morris; Thomas R Webb
Journal:  Medchemcomm       Date:  2011-01-01       Impact factor: 3.597

5.  Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers.

Authors:  Yikang Wu; Jia-Hui Huang; Xin Shen; Qi Hu; Chao-Jun Tang; Liang Li
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

6.  Synthesis of the macrocyclic core of (-)-pladienolide B.

Authors:  Philip R Skaanderup; Thomas Jensen
Journal:  Org Lett       Date:  2008-05-30       Impact factor: 6.005

7.  Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. I. Taxonomy, fermentation, isolation and screening.

Authors:  Takashi Sakai; Tomohiro Sameshima; Motoko Matsufuji; Naoto Kawamura; Kazuyuki Dobashi; Yoshiharu Mizui
Journal:  J Antibiot (Tokyo)       Date:  2004-03       Impact factor: 2.649

8.  Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. III. In vitro and in vivo antitumor activities.

Authors:  Yoshiharu Mizui; Takashi Sakai; Masao Iwata; Toshimitsu Uenaka; Kiyoshi Okamoto; Hajime Shimizu; Takao Yamori; Kentaro Yoshimatsu; Makoto Asada
Journal:  J Antibiot (Tokyo)       Date:  2004-03       Impact factor: 2.649

9.  Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. II. Physico-chemical properties and structure elucidation.

Authors:  Takashi Sakai; Naoki Asai; Akifumi Okuda; Naoto Kawamura; Yoshiharu Mizui
Journal:  J Antibiot (Tokyo)       Date:  2004-03       Impact factor: 2.649

10.  Splicing factor SF3b as a target of the antitumor natural product pladienolide.

Authors:  Yoshihiko Kotake; Koji Sagane; Takashi Owa; Yuko Mimori-Kiyosue; Hajime Shimizu; Mai Uesugi; Yasushi Ishihama; Masao Iwata; Yoshiharu Mizui
Journal:  Nat Chem Biol       Date:  2007-07-22       Impact factor: 15.040
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  15 in total

1.  Design and Synthesis of 1,2-Deoxy-pyranose Derivatives of Spliceostatin A toward Prostate Cancer Treatment.

Authors:  Yusuke Yoshikawa; Airi Ishibashi; Tsunayoshi Takehara; Takeyuki Suzuki; Kenichi Murai; Yasufumi Kaneda; Keisuke Nimura; Mitsuhiro Arisawa
Journal:  ACS Med Chem Lett       Date:  2020-05-01       Impact factor: 4.345

2.  Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome.

Authors:  Arun K Ghosh; Zhi-Hua Chen
Journal:  Org Lett       Date:  2013-09-19       Impact factor: 6.005

3.  An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921.

Authors:  Arun K Ghosh; Samuel Rodriguez
Journal:  Tetrahedron Lett       Date:  2016-05-18       Impact factor: 2.415

Review 4.  A Challenging Pie to Splice: Drugging the Spliceosome.

Authors:  Brian León; Manoj K Kashyap; Warren C Chan; Kelsey A Krug; Januario E Castro; James J La Clair; Michael D Burkart
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-15       Impact factor: 15.336

Review 5.  Modulating splicing with small molecular inhibitors of the spliceosome.

Authors:  Kerstin A Effenberger; Veronica K Urabe; Melissa S Jurica
Journal:  Wiley Interdiscip Rev RNA       Date:  2016-07-21       Impact factor: 9.957

6.  Stabilized cyclopropane analogs of the splicing inhibitor FD-895.

Authors:  Reymundo Villa; Manoj Kumar Kashyap; Deepak Kumar; Thomas J Kipps; Januario E Castro; James J La Clair; Michael D Burkart
Journal:  J Med Chem       Date:  2013-08-21       Impact factor: 7.446

Review 7.  The spliceosome as a target of novel antitumour drugs.

Authors:  Sophie Bonnal; Luisa Vigevani; Juan Valcárcel
Journal:  Nat Rev Drug Discov       Date:  2012-11       Impact factor: 84.694

8.  Coherence between cellular responses and in vitro splicing inhibition for the anti-tumor drug pladienolide B and its analogs.

Authors:  Kerstin A Effenberger; David D Anderson; Walter M Bray; Beth E Prichard; Nianchun Ma; Matthew S Adams; Arun K Ghosh; Melissa S Jurica
Journal:  J Biol Chem       Date:  2013-12-03       Impact factor: 5.157

9.  Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives.

Authors:  Chandraiah Lagisetti; Maria V Yermolina; Lalit Kumar Sharma; Gustavo Palacios; Brett J Prigaro; Thomas R Webb
Journal:  ACS Chem Biol       Date:  2013-12-30       Impact factor: 5.100

10.  Herboxidiene Features That Mediate Conformation-Dependent SF3B1 Interactions to Inhibit Splicing.

Authors:  Adriana Gamboa Lopez; Srinivasa Rao Allu; Patricia Mendez; Guddeti Chandrashekar Reddy; Hannah M Maul-Newby; Arun K Ghosh; Melissa S Jurica
Journal:  ACS Chem Biol       Date:  2021-02-22       Impact factor: 5.100
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