Literature DB >> 19434636

Stereodivergent synthesis of 17-alpha and 17-beta-alpharyl steroids: application and biological evaluation of D-ring cortistatin analogues.

Jun Shi1, Hiroki Shigehisa, Carlos A Guerrero, Ryan A Shenvi, Chuang-Chuang Li, Phil S Baran.   

Abstract

One stereocenter makes all the difference: The synthesis and biological evaluation of 17-epi-cortistatin A is reported from a common intermediate used to procure natural cortistatin A. The synthesis features a unique stereocontrolled Raney-Ni reduction process that can be employed to reliably produce both alpha- and beta-configured D-ring aryl steroids. Biological evaluations of these "cortalogs" are reported for the first time.

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Year:  2009        PMID： 19434636      PMCID： PMC3495592          DOI： 10.1002/anie.200901116

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  15 in total

Review 1.  The value of natural products to future pharmaceutical discovery.

Authors:  Dwight D Baker; Min Chu; Uma Oza; Vineet Rajgarhia
Journal:  Nat Prod Rep       Date:  2007-05-09       Impact factor: 13.423

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.  A concise synthesis of the pentacyclic framework of cortistatins.

Authors:  Shuji Yamashita; Kentaro Iso; Masahiro Hirama
Journal:  Org Lett       Date:  2008-07-17       Impact factor: 6.005

6.  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

7.  A short, scalable synthesis of the carbocyclic core of the anti-angiogenic cortistatins from (+)-estrone by B-ring expansion.

Authors:  László Kürti; Barbara Czakó; E J Corey
Journal:  Org Lett       Date:  2008-10-30       Impact factor: 6.005

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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  14 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  Formal total synthesis of (±)-cortistatin A.

Authors:  Eric M Simmons; Alison R Hardin-Narayan; Xuelei Guo; Richmond Sarpong
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

3.  Synthetic studies toward (+)-cortistatin A.

Authors:  Zhang Wang; Mingji Dai; Peter K Park; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2011-10-29       Impact factor: 2.457

4.  An analog of the natural steroidal alkaloid cortistatin A potently suppresses Tat-dependent HIV transcription.

Authors:  Guillaume Mousseau; Mark A Clementz; Wendy N Bakeman; Nisha Nagarsheth; Michael Cameron; Jun Shi; Phil Baran; Rémi Fromentin; Nicolas Chomont; Susana T Valente
Journal:  Cell Host Microbe       Date:  2012-07-19       Impact factor: 21.023

5.  Creation of readily accessible and orally active analogue of cortistatin a.

Authors:  Naoyuki Kotoku; Yuji Sumii; Takeshi Hayashi; Satoru Tamura; Takashi Kawachi; Sho Shiomura; Masayoshi Arai; Motomasa Kobayashi
Journal:  ACS Med Chem Lett       Date:  2012-07-10       Impact factor: 4.345

6.  Scalable synthesis of cortistatin A and related structures.

Authors:  Jun Shi; Georg Manolikakes; Chien-Hung Yeh; Carlos A Guerrero; Ryan A Shenvi; Hiroki Shigehisa; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

7.  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

8.  Synthesis of cortistatins A, J, K and L.

Authors:  Alec N Flyer; Chong Si; Andrew G Myers
Journal:  Nat Chem       Date:  2010-08-01       Impact factor: 24.427

9.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

10.  Cyclin-dependent kinase 8 mediates chemotherapy-induced tumor-promoting paracrine activities.

Authors:  Donald C Porter; Elena Farmaki; Serena Altilia; Gary P Schools; Deborah K West; Mengqian Chen; Bey-Dih Chang; Anatoliy T Puzyrev; Chang-uk Lim; Rebecca Rokow-Kittell; Lawrence T Friedhoff; Athanasios G Papavassiliou; Swathi Kalurupalle; Gregory Hurteau; Jun Shi; Phil S Baran; Balazs Gyorffy; Mark P Wentland; Eugenia V Broude; Hippokratis Kiaris; Igor B Roninson
Journal:  Proc Natl Acad Sci U S A       Date:  2012-08-06       Impact factor: 11.205
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