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Synlett 2008(14): 2093-2096  
DOI: 10.1055/s-2008-1078251
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Synthetic Approach to the Communesins

Jonathan H. George, Robert M. Adlington*
Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, UK
Fax: +44(1865)275632; e-Mail: robert.adlington@chem.ox.ac.uk;
Further Information

Publication History

Received 30 May 2008
Publication Date:
05 August 2008 (online)

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Abstract

A synthetic approach to the communesin family of ­indole alkaoids has been investigated, with a cascade reaction sequence involving formation of a transient 1-alkoxycarbonyl­imidazole intermediate and subsequent addition onto an indole as the key step.

Key words

alkaloids - indoles - cascade reactions - heterocycles - communesins

    References and Notes

  • 1a Numata A. Takahashi C. Ito Y. Takada T. Kawai K. Usami Y. Matsumura E. Imachi M. Ito T. Hasegawa T. Tetrahedron Lett.  1993,  34:  2355 
    Google Scholar
  • 1b Jadulco R. Edrada RA. Ebel R. Berg A. Schaumann K. Wray V. Steube K. Proksch P. J. Nat. Prod.  2004,  67:  78 
    Google Scholar
  • 1c Hayashi H. Matsumoto H. Akiyama K. Biosci., Biotechnol., Biochem.  2004,  68:  753 
    Google Scholar
  • 1d Dalsgaard PW. Blunt JW. Munro MHG. Frisvad JC. Christophersen C. J. Nat. Prod.  2005,  68:  258 
    Google Scholar
  • 2 Wigley LJ. Mantle PG. Perry DA. Phytochemistry  2006,  67:  561 
    CrossrefGoogle Scholar
  • 3a Yang J. Wu H. Shen L. Qin Y. J. Am. Chem. Soc.  2007,  129:  13794 
    Google Scholar
  • 3b Yang J. Song H. Xiao X. Wang J. Qin Y. Org. Lett.  2006,  8:  2187 
    Google Scholar
  • 4a May JA. Zeidan RK. Stoltz BM. Tetrahedron. Lett.  2003,  44:  1203 
    Google Scholar
  • 4b Crawley SL. Funk RL. Org. Lett.  2003,  5:  3169 
    Google Scholar
  • 4c Crawley SL. Funk RL. Org. Lett.  2006,  8:  3995 
    Google Scholar
  • 4d Seo JH. Artman GD. Weinreb SM. J. Org. Chem.  2006,  71:  8891 
    Google Scholar
  • 5 Verbitski SM. Mayne CL. Davis RA. Concepcion GP. Ireland CM. J. Org. Chem.  2002,  67:  7124 
    CrossrefGoogle Scholar
  • 6a Fuchs JR. Funk RL. J. Am. Chem. Soc.  2004,  126:  5068 
    Google Scholar
  • 6b Sabahi A. Novikov A. Ranier JD. Angew. Chem. Int. Ed.  2006,  45:  4317 
    Google Scholar
  • 7 Wojciechowski K. Eur. J. Org. Chem.  2001,  3587 
    Google Scholar
  • 8a Bowen RD. Davies DE. Fishwick CWG. Glasbey TO. Noyce SJ. Storr RC. Tetrahedron Lett.  1982,  23:  4501 
    Google Scholar
  • 8b Hodgetts I. Noyce SJ. Storr RC. Tetrahedron Lett.  1984,  25:  545 
    Google Scholar
  • 8c Fishwick CWG. Storr RC. Manley PW. J. Chem. Soc., Chem. Commun.  1984,  1304 
    Google Scholar
  • 8d Consonni R. Croce PD. Ferraccioli R. La Rosa C. J. Chem. Soc., Perkin Trans. 1  1996,  1809 
    Google Scholar
  • 10 Njar VCO. Synthesis  2000,  2019 
    Article in Thieme ConnectGoogle Scholar
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Crystal structure obtained for compound 20. CCDC 689636 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.