Literature DB >> 22879684

Synthetic studies toward (+)-cortistatin A.

Zhang Wang1, Mingji Dai, Peter K Park, Samuel J Danishefsky.   

Abstract

We describe herein the synthesis of a late-stage intermediate en route to cortistatin A. Key transformations included a Snieckus-like cascade sequence culminating in a 6π-electrocyclization, an alkylative dearomatization, and the stereoselective functionalization of the cortistatin A-ring. While the total synthesis we sought was not accomplished, the work sets the stage for several approaches to the preparation of novel analogs via diverted total synthesis.

Entities:  

Year:  2011        PMID: 22879684      PMCID: PMC3413295          DOI: 10.1016/j.tet.2011.10.026

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  44 in total

Review 1.  On the remarkable antitumor properties of fludelone: how we got there.

Authors:  Alexey Rivkin; Ting-Chao Chou; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-06       Impact factor: 15.336

2.  Cortistatins A, B, C, and D, anti-angiogenic steroidal alkaloids, from the marine sponge Corticium simplex.

Authors:  Shunji Aoki; Yasuo Watanabe; Mami Sanagawa; Andi Setiawan; Naoyuki Kotoku; Motomasa Kobayashi
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419

3.  Enantioselective synthesis of (+)-cortistatin a, a potent and selective inhibitor of endothelial cell proliferation.

Authors:  Hong Myung Lee; Cristina Nieto-Oberhuber; Matthew D Shair
Journal:  J Am Chem Soc       Date:  2008-12-17       Impact factor: 15.419

4.  Rapid construction of the cortistatin pentacyclic core.

Authors:  Eric M Simmons; Alison R Hardin; Xuelei Guo; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Total synthesis of (+)-cortistatin A.

Authors:  K C Nicolaou; Ya-Ping Sun; Xiao-Shui Peng; Damien Polet; David Y-K Chen
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.

Authors:  E J Alvarez-Manzaneda; R Chahboun; I Barranco Pérez; E Cabrera; E Alvarez; R Alvarez-Manzaneda
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

7.  Total synthesis of the quinone epoxide dimer (+)-torreyanic acid: application of a biomimetic oxidation/electrocyclization/Diels-Alder dimerization cascade.

Authors:  Chaomin Li; Richard P Johnson; John A Porco
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

8.  Structure-activity relationship and biological property of cortistatins, anti-angiogenic spongean steroidal alkaloids.

Authors:  Shunji Aoki; Yasuo Watanabe; Daiki Tanabe; Masayoshi Arai; Hideaki Suna; Katsushiro Miyamoto; Hiroshi Tsujibo; Kazutake Tsujikawa; Hiroshi Yamamoto; Motomasa Kobayashi
Journal:  Bioorg Med Chem       Date:  2007-08-21       Impact factor: 3.641

9.  A novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition and its application in the synthesis of the cortistatin core.

Authors:  Mingji Dai; Zhang Wang; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2008-11-17       Impact factor: 2.415

10.  Synthesis of (+)-cortistatin A.

Authors:  Ryan A Shenvi; Carlos A Guerrero; Jun Shi; Chuang-Chuang Li; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419

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  3 in total

1.  Synthesis of the Cortistatin Pentacyclic Core by Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling.

Authors:  Claudio Aquino; Stephen N Greszler; Glenn C Micalizio
Journal:  Org Lett       Date:  2016-05-19       Impact factor: 6.005

2.  The domestication of ortho-quinone methides.

Authors:  Wen-Ju Bai; Jonathan G David; Zhen-Gao Feng; Marisa G Weaver; Kun-Liang Wu; Thomas R R Pettus
Journal:  Acc Chem Res       Date:  2014-12-03       Impact factor: 22.384

3.  Didehydro-Cortistatin A Inhibits HIV-1 by Specifically Binding to the Unstructured Basic Region of Tat.

Authors:  Sonia Mediouni; Krishna Chinthalapudi; Mary K Ekka; Ippei Usui; Joseph A Jablonski; Mark A Clementz; Guillaume Mousseau; Jason Nowak; Venkat R Macherla; Jacob N Beverage; Eduardo Esquenazi; Phil Baran; Ian Mitchelle S de Vera; Douglas Kojetin; Erwann P Loret; Kendall Nettles; Souvik Maiti; Tina Izard; Susana T Valente
Journal:  mBio       Date:  2019-02-05       Impact factor: 7.867

  3 in total

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