PDF icon PDF herunterladen
Synthesis 2012(1): 125-129  
DOI: 10.1055/s-0031-1289627
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Phenanthridine Analogue of Natural Isocarbostyril Alkaloids

Andrea R. Martíneza, Daniel R. Vegab, José M. Aguirrec, Beatriz Lantañoa,c, Graciela Y. Moltrasio*a
a Cátedra de Química Orgánica III, Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
Fax: +54(11)49648252; e-Mail: gmoltra@ffyb.uba.ar;
b Unidad de Actividad Física, Comisión Nacional de Energía Atómica, Avenida Gral. Paz 1499, 1650 San Martín, Buenos Aires, Argentina
c Departamento de Ciencias Básicas, Universidad Nacional de Luján, Luján, Argentina
Weitere Informationen

Publikationsverlauf

Received 27 September 2011
Publikationsdatum:
01. Dezember 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

A phenanthridine alkaloid analogue has been synthesized by a short sequence, using a stereoselective hydroxylation process and a Pictet-Spengler reaction. The starting material, 5-(3,4-dimethoxyphenyl)-6-nitrocyclohex-2-enol, is a compound previously reported by us and prepared through a Diels-Alder reaction. The configurational assignment of the starting material, previously done by NMR experiments, was confirmed by X-ray crystallographic analysis.

Key words

phenanthridine alkaloids - stereoselective hydroxylation - Pictet-Spengler reaction - heterocycles - cyclizations

    References

  • 1 Koehn FE. Carter GT. Nat. Rev. Drug Discovery  2005,  4:  206 
    Suche in Google Scholar
  • 2 Newman DJ. Cragg GM. J. Nat. Prod.  2007,  70:  461 
    Suche in Google Scholar
  • 3 Mann J. Nat. Rev. Cancer  2002,  2:  143 
    Suche in Google Scholar
  • 4 Altmann KH. Gertsch J. Nat. Prod. Rep.  2007,  24:  327 
    Suche in Google Scholar
  • 5 Ingrassia L. Lefranc F. Dewelle J. Pottier L. Mathieu V. Spiegl-Kreinecker S. Sauvage S. El Yazidi M. Dehoux M. Berger W. Van Quaquebeke E. Kiss R. J. Med. Chem.  2009,  52:  1100 
    Suche in Google Scholar
  • 6 Kornienko A. Evidente A. Chem. Rev.  2008,  108:  1982 
    Suche in Google Scholar
  • 7 Ingrassia L. Lefranc F. Mathieu V. Darro F. Kiss R. Transl. Oncol.  2008,  1:  1 
    Suche in Google Scholar
  • 8 Pettit GR. Gaddamidi V. Herald DL. Singh SB. Cragg GM. Schmidt JM. Boettner FE. Williams M. Sagawa Y. J. Nat. Prod.  1986,  49:  995 
    Suche in Google Scholar
  • 9 Pettit GR. Pettit GR. Backhaus RA. Boyd MR. Meerow AW. J. Nat. Prod.  1993,  56:  1682 
    Suche in Google Scholar
  • 10 Danishefsky J. Lee JY. J. Am. Chem. Soc.  1989,  111:  4829 
    Suche in Google Scholar
  • 11 Keck GE. McHardy SF. Murry JA. J. Am. Chem. Soc.  1995,  117:  7289 
    Suche in Google Scholar
  • 12 Tian X. Hudlicky T. Königsberger K. J. Am. Chem. Soc.  1995,  117:  3643 
    Suche in Google Scholar
  • 13 Trost BM. Pulley SR. J. Am. Chem. Soc.  1995,  117:  10143 
    Suche in Google Scholar
  • 14 Hudlicky JK. Tian X. Königsberger K. Maurya R. Rouden J. Fan B. J. Am. Chem. Soc.  1996,  118:  10752 
    Suche in Google Scholar
  • 15 Keck GE. Wager TT. J. Org. Chem.  1996,  61:  8366 
    Suche in Google Scholar
  • 16 Doyle TJ. Hendrix M. VanDerveer D. Javanmard S. Haseltine J. Tetrahedron  1997,  53:  11153 
    Suche in Google Scholar
  • 17 Magnus P. Sebhat JK. Tetrahedron  1998,  54:  15509 
    Suche in Google Scholar
  • 18 Keck GE. Wager TT. McHardy SF. J. Org. Chem.  1998,  63:  9164 
    Suche in Google Scholar
  • 19 Keck GE. McHardy SF. Murry JA. J. Org. Chem.  1999,  64:  4465 
    Suche in Google Scholar
  • 20 Keck GE. Wager TT. Rodriquez JFD. J. Am. Chem. Soc.  1999,  121:  5176 
    Suche in Google Scholar
  • 21 Rigby JH. Maharoof USM. Mateo ME. J. Am. Chem. Soc.  2000,  122:  6624 
    Suche in Google Scholar
  • 22 Aceña JL. Arjona O. León ML. Plumet J. Org. Lett.  2000,  2:  3683 
    Suche in Google Scholar
  • 23 Martínez AR. Moltrasio Iglesias GY. J. Chem. Res., Synop.  1998,  169 ; J. Chem. Res., Miniprint 1998, 853
  • 24 Hill RK. Joule JA. Loeffler LJ. J. Am. Chem. Soc.  1962,  84:  4951 
    Suche in Google Scholar
  • 25 Cremer D. Pople JA. J. Am. Chem. Soc.  1975,  97:  1354 
    Suche in Google Scholar
  • 26 Hoveyda AH. Evans DA. Fu GC. Chem. Rev.  1993,  93:  1307 
    Suche in Google Scholar
  • 27 Bartlett PD. Rec. Chem. Prog.  1957,  18:  111 
    Suche in Google Scholar
  • 28 Fieser LF. Fieser M. In Reagents for Organic Synthesis   Vol. 1:  John Wiley & Sons; New York: 1967.  p.796 
    Suche in Google Scholar
  • 29 Murphy DK. Alumbaugh RL. Rickborn B. J. Am. Chem. Soc.  1969,  91:  2649 
    Suche in Google Scholar
  • 30 El-Fishawy AM. Slatkin JE. Knapp JE. Schiff PL. J. Pharm. Sci.  1984,  73:  1639 
    Suche in Google Scholar
  • 31 McKitterick BA. Ganem B. J. Org. Chem.  1985,  50:  5897 
    Suche in Google Scholar
  • 32 XPREP - The automatic space group determination program in SHELXL. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997
  • 33 North AC. Philips DC. Mathews FS. Acta Crystallogr., Sect. A  1968,  2:  351 
    Suche in Google Scholar