Literature DB >> 18630922

A concise synthesis of the pentacyclic framework of cortistatins.

Shuji Yamashita1, Kentaro Iso, Masahiro Hirama.   

Abstract

An efficient synthesis of the pentacyclic framework of cortistatins has been developed. The key strategy comprises assembly of the A- and the CD-ring fragments by Knoevenagel reaction, facile formation of the pyran ring via electrocyclization, and construction of the seven-membered B-ring by radical addition to an alpha,beta-unsaturated ketone.

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Year:  2008        PMID： 18630922     DOI： 10.1021/ol8012099

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


  18 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.  Total synthesis of (±)-phomactin A. Lessons learned from respecting a challenging structural topology.

Authors:  Grant S Buchanan; Kevin P Cole; Yu Tang; Richard P Hsung
Journal:  J Org Chem       Date:  2011-08-05       Impact factor: 4.354

3.  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

4.  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

5.  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

6.  Chemoselectivity: the mother of invention in total synthesis.

Authors:  Ryan A Shenvi; Daniel P O'Malley; Phil S Baran
Journal:  Acc Chem Res       Date:  2009-04-21       Impact factor: 22.384

7.  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

8.  A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.

Authors:  Jessica L Frie; Christopher S Jeffrey; Erik J Sorensen
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

9.  A concise synthesis of the cortistatin core.

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

10.  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
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