PDF icon PDF herunterladen
Synlett 2011(15): 2211-2213  
DOI: 10.1055/s-0030-1261184
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Concise Synthesis of 1,4a-Bifunctionalised Decalin Building Blocks by C-H Activation of Decalin

Mario Uosis-Martin, Mary F. Mahon, Maksims Yevglevskis, Simon E. Lewis*
Department of Chemistry, University of Bath, Bath, BA2 7AY, UK
Fax: +44(1225)386231; e-Mail: s.e.lewis@bath.ac.uk;
Weitere Informationen

Publikationsverlauf

Received 17 May 2011
Publikationsdatum:
12. August 2011 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

Friedel-Crafts acylation of decalin introduces functionality at C1 and C4a, which may be elaborated to novel building blocks possessing a methyl ketone, methyl carbinol, or vinyl group at the ring junction.

Key words

hydrocarbons - acylation - bicyclic compounds - alkenes - Wittig reaction

    References

  • 1a Hanson JR. Nat. Prod. Rep.  2010,  27:  887 
    Suche in Google Scholar
  • 1b Ibrahim-Ouali M. Steroids  2009,  74:  133 
    Suche in Google Scholar
  • 1c Ibrahim-Ouali M. Steroids  2008,  73:  775 
    Suche in Google Scholar
  • 1d Ibrahim-Ouali M. Steroids  2008,  73:  375 
    Suche in Google Scholar
  • 1e Nising CF. Bräse S. Angew. Chem. Int. Ed.  2008,  47:  9389 
    Suche in Google Scholar
  • 1f Ibrahim-Ouali M. Steroids  2007,  72:  475 
    Suche in Google Scholar
  • 1g Ibrahim-Ouali M. Santelli M. Steroids  2006,  71:  1025 
    Suche in Google Scholar
  • 2a Maimone TJ. Baran PS. Nat. Chem. Biol.  2007,  3:  396 
    Suche in Google Scholar
  • 2b Yoder RA. Johnston JN. Chem. Rev.  2005,  105:  4730 
    Suche in Google Scholar
  • 2c Tokoroyama T. Synthesis  2000,  611 
  • 3a Singh V. Iyer SR. Pal S. Tetrahedron  2005,  61:  9197 
    Suche in Google Scholar
  • 3b Mulzer J. Castagnolo D. Felzmann W. Marchart S. Pilger C. Enev VS. Chem. Eur. J.  2006,  12:  5992 
    Suche in Google Scholar
  • 3c Liao C.-C. Pure Appl. Chem.  2005,  77:  1221 
    Suche in Google Scholar
  • 4 Varner MA. Grossman RB. Tetrahedron  1999,  55:  13867 
    CrossrefSuche in Google Scholar
  • 5 Buchbauer G. Spreitzer H. Supp B. Chem.-Ztg.  1988,  112:  319 
    Suche in Google Scholar
  • 6a Baddeley G. Wrench E. J. Chem. Soc.  1959,  1324 
  • 6b Ahmad MS. Baddeley G. Heaton BG. Rasburn JW. Proc. Chem. Soc.  1959,  395 
  • 6c Baddeley G. Heaton BG. Rasburn JW. J. Chem. Soc.  1960,  4713 
  • 6d Baddeley G. Heaton BG. Rasburn JW. J. Chem. Soc.  1961,  3828 
  • 6e Baddeley G. Heaton BG. Rasburn JW. J. Chem. Soc.  1961,  3835 
  • 7a Vol’pin ME. Akhrem IS. Orlinkov AV. New J. Chem.  1989,  13:  771 
    Suche in Google Scholar
  • 7b Gallo R. Lazzeri V. Appl. Catal. A  1996,  146:  87 
    Suche in Google Scholar
  • 8a Tabushi I. Fujita K. Oda R. Tetrahedron Lett.  1968,  9:  4247 
    Suche in Google Scholar
  • 8b Tabushi I. Fujita K. Oda R. Tetrahedron Lett.  1968,  9:  5455 
    Suche in Google Scholar
  • 8c Tabushi I. Fujita K. Oda R. Tetrahedron Lett.  1969,  10:  2581 
    Suche in Google Scholar
  • 8d Groves JK. Jones N. J. Chem. Soc. C  1969,  608 
  • 8e Tavares RF. Dorsky J. Easter WM. J. Org. Chem.  1971,  36:  2434 
    Suche in Google Scholar
  • 8f Pardo R. Santelli M. Tetrahedron Lett.  1981,  22:  3843 
    Suche in Google Scholar
  • 8g Akhrem IS. Orlinkov AV. Mysov EI. Vol’pin ME. Tetrahedron Lett.  1981,  22:  3891 
    Suche in Google Scholar
  • 8h Harding KE. Clement KS. Gilbert JC. Wiechman B. J. Org. Chem.  1984,  49:  2049 
    Suche in Google Scholar
  • 8i Ha H.-J. Park K.-P. Bull. Korean Chem. Soc.  1988,  9:  411 
    Suche in Google Scholar
  • 8j Morel-Fourrier C. Dulcère J.-P. Santelli M. J. Am. Chem. Soc.  1991,  113:  8062 
    Suche in Google Scholar
  • 8k Davison GR. Howard JAK. Pitchford NA. Jones AM. Rasburn JW. Simpson AJ. Tetrahedron  1993,  49:  10123 
    Suche in Google Scholar
  • 9a Fields R. Holt G. Orabi MOA. Naseeri-Noori B. J. Chem. Soc., Perkin Trans. 1  1979,  233 
  • 9b Ndandji C. Tsuchiya-Aikawa L. Gallo R. Metzger J. Desbois M. New J. Chem.  1982,  6:  137 
    Suche in Google Scholar
  • 10a Baddeley G. Hulme P. J. Chem. Soc.  1965,  5148 
  • 10b Swallow DL. Edwards PN. Finter NB. Ann. N.Y. Acad. Sci.  1970,  173:  292 
    Suche in Google Scholar
11

Compound 6: CCDC #824429. 11: CCDC #824430.