Download PDF
Synthesis 2011(23): 3887-3893  
DOI: 10.1055/s-0030-1260258
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Vitamin D Heterocyclic Analogues; Part 2: Synthesis of the First Vitamin D Analogues with a Tetrazole Ring at the Side Chain

Zoila Gándara, Pedro Lois Suárez, Maria González, Generosa Gómez*, Yagamare Fall*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain
Fax: +34(98)6812262; e-Mail: yagamare@uvigo.es; e-Mail: ggomez@uvigo.es;
Further Information

Publication History

Received 2 August 2011
Publication Date:
07 October 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

Access to the calcitriol analogues with a tetrazole ring at the side chain was very efficiently achieved using the Calverley-Choudhry approach instead of the Wittig-Horner method, which gave very low yields.

Key words

1α,25-dihydroxyvitamin D3 - tetrazole - heterocycles - azasteroids - Windhaus-Grundmann ketone

    References

  • 1 Bouillon R. Okamura WH. Norman AW. Endocr. Rev.  1995,  16:  200 
    CrossrefPubMedSearch in Google Scholar
  • For general reviews on vitamin D chemistry and biology, see:
  • 2a Vitamin D: Chemistry, Biology and Clinical Applications of the Steroid Hormone   Norman AW. Bouillon R. Thomasset M. Vitamin D Workshop, Inc.; Riverside (CA, USA): 1997. 
  • 2b Feldman D. Glorieux FH. Pike JW. Vitamin D   Academic Press; San Diego: 1997. 
  • 2c Pardo R. Santelli M. Bull. Soc. Chim. Fr.  1985,  98 
  • 2d Dai H. Posner GH. Synthesis  1994,  1383 
  • 2e Zhu G.-D. Okamura WH. Chem. Rev.  1995,  95:  1877 
    Search in Google Scholar
  • 3a Oves D. Ferrero M. Fernández S. Gotor V. J. Org. Chem.  2003,  68:  1154 ; and references cited therein
    Search in Google Scholar
  • 3b Silverman SM. Jeon HB. Posner GH. Suh B.-C. Tetrahedron Lett.  2004,  45:  4623 
    Search in Google Scholar
  • 4a Fall Y. Barreiro C. Fernández C. Mouriño A. Tetrahedron Lett.  2002,  43:  1433 
    Search in Google Scholar
  • 4b

    Fall Y., Puente M., Gómez G., Bolaño T., Suarez P. L., Gándara Z.; Abstracts of the 12th Workshop on Vitamin D; Maastricht, The Netherlands, July 6-7, 2003.

  • 4c

    Gómez G., Suarez P. L., Sáa C., Fall Y., Puente M.; Abstracts of the 12th Workshop on Vitamin D; Maastricht, The Netherlands, July 6-7, 2003.

  • 4d Suárez PL. Gándara Z. Gómez G. Fall Y. Tetrahedron Lett.  2004,  45:  4619 
    Search in Google Scholar
  • 4e Sestelo JP. de Uña O. Mouriño A. Sarandeses LA. Synlett  2002,  719 
  • 4f Fernández-Gacio A. Mouriño A. Eur. J. Org. Chem.  2002,  2529 
  • 5 Pérez-Sestelo J. Mascareñas JL. Castedo L. Mouriño A. J. Org. Chem.  1993,  58:  118 
    CrossrefSearch in Google Scholar
  • 6 Mouriño A. Torneiro M. Vitale C. Fernandez S. Perez-Sestelo J. Anne S. Gregorio C. Tetrahedron Lett.  1997,  33:  4713 
    Search in Google Scholar
  • 7 Posner GH. Nelson TD. Guyton KZ. Kensler TW. J. Med. Chem.  1992,  35:  3280 
    CrossrefSearch in Google Scholar
  • 8 Regarding discrimination of structural isomers of N-substi-tuted tetrazoles, see: Sveshnikov NN. Nelson JH. Magn. Reson. Chem.  1997,  35:  209 
    CrossrefSearch in Google Scholar
  • 9a Andrews DR. Barton DHR. Hesse RH. Pechet MM. J. Org. Chem.  1986,  51:  4819 ; and references cited therein
    Search in Google Scholar
  • 9b Calverley MJ. Tetrahedron  1987,  43:  4609 
    Search in Google Scholar
  • 9c Choudhry SC. Belica PS. Coffen DL. Focella A. Maehr H. Manchand PS. Serico L. Yang RT. J. Org. Chem.  1993,  58:  1496 
    Search in Google Scholar