Literature DB >> 19924219

A concise synthesis of the cortistatin core.

Mingji Dai1, Samuel J Danishefsky.   

Abstract

We describe a concise and convergent route to the core matrix of the cortistatin steroidal alkaloids. The salient features of the synthesis are the Snieckus cascade methodology and the Masamune alkylative dearomatization. This chemistry lends itself to a total synthesis of the cortistatins and to the development of a SAR program based on diverted total synthesis.

Entities:  

Year:  2008        PMID: 19924219      PMCID: PMC2598409          DOI: 10.1016/j.tetlet.2008.09.018

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  18 in total

1.  Discovery of potent cell migration inhibitors through total synthesis: lessons from structure-activity studies of (+)-migrastatin.

Authors:  Jón T Njardarson; Christoph Gaul; Dandan Shan; Xin-Yun Huang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2004-02-04       Impact factor: 15.419

Review 2.  Angiogenesis.

Authors:  J Folkman; Y Shing
Journal:  J Biol Chem       Date:  1992-06-05       Impact factor: 5.157

Review 3.  Small molecule natural products in the discovery of therapeutic agents: the synthesis connection.

Authors:  Rebecca M Wilson; Samuel J Danishefsky
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

4.  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

5.  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

6.  Heteroatom influence on the pi-facial selectivity of Diels-Alder cycloadditions to 1-oxa-4-thia-6-vinylspiro[4.5]dec-6-ene, 3-methoxy-3-methyl-2-vinylcyclohexene, and 3-methoxy-2-vinylcyclohexene.

Authors:  Veejendra K Yadav; Govindaraji Senthil; K Ganesh Babu; Masood Parvez; Jennifer Lee Reid
Journal:  J Org Chem       Date:  2002-02-22       Impact factor: 4.354

7.  A modular approach to structurally diverse bidentate chelate ligands for transition metal catalysis

Authors: 
Journal:  Chemistry       Date:  2000-08-04       Impact factor: 5.236

8.  Palladium-catalyzed carbonylative cyclization of unsaturated aryl iodides and dienyl triflates, iodides, and bromides to indanones and 2-cyclopentenones.

Authors:  Steve V Gagnier; Richard C Larock
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419

9.  Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues.

Authors:  Amos B Smith; Jeffrey B Sperry; Qiang Han
Journal:  J Org Chem       Date:  2007-08-08       Impact factor: 4.354

10.  A simple and advantageous protocol for the oxidation of alcohols with O-iodoxybenzoic acid (IBX).

Authors:  Jesse D More; Nathaniel S Finney
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

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

Authors:  Mark G Nilson; Raymond L Funk
Journal:  J Am Chem Soc       Date:  2011-07-21       Impact factor: 15.419

5.  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

6.  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

7.  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

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.  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

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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