Literature DB >> 21165151

Studies towards the synthesis of the marine alkaloid chartelline C.

Phillip J Black1, Evan A Hecker, Philip Magnus.   

Abstract

The 2,6-dibromoindole 5 underwent regioselective Sonogashira coupling at the 2 position with simple acetylenic partners. While, the imidazole-acetylene 16 failed to couple to 5, the cyclic carbonate 19 succeeded to give 20, which was further elaborated into the indole-imidazole 23.

Entities:  

Year:  2007        PMID: 21165151      PMCID: PMC3001619          DOI: 10.1016/j.tetlet.2007.07.040

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


  6 in total

1.  A remarkable ring contraction en route to the chartelline alkaloids.

Authors:  Phil S Baran; Ryan A Shenvi; Christos A Mitsos
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-13       Impact factor: 15.336

2.  Construction of beta-haloenamides via direct copper-promoted coupling of lactams with 2-chloro and 2-bromo vinyliodides.

Authors:  Cuixiang Sun; Jason E Camp; Steven M Weinreb
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

3.  Beta-hydroxy-gamma-lactones as chiral building blocks for the enantioselective synthesis of marine natural products.

Authors:  C García; T Martín; V S Martín
Journal:  J Org Chem       Date:  2001-02-23       Impact factor: 4.354

4.  Total synthesis of (+/-)-chartelline C.

Authors:  Phil S Baran; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2006-11-01       Impact factor: 15.419

5.  Explorations on the total synthesis of the unusual marine alkaloid chartelline A.

Authors:  Cuixiang Sun; Xichen Lin; Steven M Weinreb
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

6.  Efficient construction of the securine A carbon skeleton.

Authors:  Peter Korakas; Stuart Chaffee; J Brad Shotwell; Pamela Duque; John L Wood
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-27       Impact factor: 11.205

  6 in total
  1 in total

1.  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

  1 in total

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