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Literature DB >> 21761900

Total synthesis of (±)-cortistatin J from furan.

Abstract

A concise, diastereoselective total synthesis of (±)-cortistatin J has been completed in 20 steps from furan. Key steps include an intramolecular [4 + 3] cyclization of a disubstituted furan with a (Z)-2-(trialkylsilyloxy)-2-enal to construct the tetracyclic core and a (Z)-vinylsilane/iminium ion cyclization to form the A ring.

Entities: Chemical Disease Gene Species

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Year: 2011 PMID： 21761900 PMCID： PMC3154988 DOI： 10.1021/ja206138d

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

32 in total

1. 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

2. 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

3. 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

4. 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

5. A model study for the concise construction of the oxapentacyclic core of cortistatins through intramolecular Diels-Alder and oxidative dearomatization-cyclization reactions.

Authors: Lianzhu Liu; Yingxiang Gao; Chao Che; Na Wu; David Zhigang Wang; Chuang-Chuang Li; Zhen Yang
Journal: Chem Commun (Camb) Date: 2008-12-09 Impact factor: 6.222

6. 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

7. 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

8. 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

9. Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach.

Authors: Gary A Molander; Noel M Ellis
Journal: J Org Chem Date: 2008-08-06 Impact factor: 4.354

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

6 in total

1. 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

2. Structure-Based Design of Type II Inhibitors Applied to Maternal Embryonic Leucine Zipper Kinase.

Authors: Christopher N Johnson; Christophe Adelinet; Valerio Berdini; Lijs Beke; Pascal Bonnet; Dirk Brehmer; Frederick Calo; Joseph E Coyle; Phillip J Day; Martyn Frederickson; Eddy J E Freyne; Ron A H J Gilissen; Christopher C F Hamlett; Steven Howard; Lieven Meerpoel; Laurence Mevellec; Rachel McMenamin; Elisabeth Pasquier; Sahil Patel; David C Rees; Joannes T M Linders
Journal: ACS Med Chem Lett Date: 2014-05-23 Impact factor: 4.345