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Synthesis 2011(21): 3563-3568  
DOI: 10.1055/s-0030-1260226
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Application of Azomethine Ylides in the Synthesis of Carbohydrate-Derived Spiroheterocycles

Piyali Deb Barman, Ishita Sanyal, Sukhendu B. Mandal, Asish Kumar Banerjee*
Department of Chemistry, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India
Fax: +91(33)24735197; e-Mail: ashisbanerjee@iicb.res.in;
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Publikationsverlauf

Received 28 June 2011
Publikationsdatum:
13. September 2011 (online)

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Abstract

A series of sugar-fused spiro-pyrrolidine, -pyrrolizidine, and -indolizidine heterocycles were synthesized through a unique application of a 1,3-dipolar cycloaddition reaction of an azomethine ylide with a carbohydrate-derived olefin. The 1,3-dipoles synthesized from secondary α-amino acids (sarcosine, proline, or pipecolinic acid) and 1,2-diketones (isatin or acenaphthoquinone), upon reaction with the olefin, gave the corresponding cycloaddition products in good-to-very good yields.

Key words

heterocycles - spiro compounds - carbohydrates - ylides - cycloadditions

    References

  • 1a Doddi VR. Kokatla HP. Pal APJ. Basak RK. Vankar YD. Eur. J. Org. Chem.  2008,  5731 
  • 1b Koester DC. Holkenbrink A. Werz DB. Synthesis  2010,  3217 
  • 1c Orth R. Pitscheider M. Sieber SA. Synthesis  2010,  2201 
  • 1d Grabosch C. Kleinert M. Lindhorst TK. Synthesis  2010,  828 
  • 1e Vecchi A. Chambery A. Chiappe C. Marra A. Dondoni A. Synthesis  2010,  2043 
  • 1f Berthold HJ. Schotten T. Hoffmann F. Thiem J. Synthesis  2010,  741 
  • 2 Calarese DA. Scanlan CN. Zwick MB. Deechongkit S. Mimura Y. Kunert R. Zhu P. Wormald MR. Stanfield RL. Roux KH. Kelly JW. Rudd PM. Dwek RA. Katinger H. Burton DR. Wilson IA. Science (Washington, D. C.)  2003,  300:  2065 
    CrossrefSuche in Google Scholar
  • 3 Barradas JS. Errea MI. Accorso NBD. Sepúlveda CS. Damonte EB. Eur. J. Org. Chem.  2011,  46:  259 
    Suche in Google Scholar
  • 4a Cipolla L. La Ferla B. Nicotra F. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates)  2003,  3:  485 
    Suche in Google Scholar
  • 4b Harris CM. Harris TM. J. Am. Chem. Soc.  1982,  104:  363 
    Suche in Google Scholar
  • 5 Hosoya T. Takashiro E. Matsumoto T. Suzuki K. Tetrahedron Lett.  1994,  35:  4591 
    CrossrefSuche in Google Scholar
  • 6 Ferguson NM. Cummings DAT. Cauchemez S. Fraser C. Riley S. Meeyai A. Iamsirithaworn S. Burke DS. Nature (London)  2005,  437:  209 
    CrossrefSuche in Google Scholar
  • 7 Kim HO. Ahn SK. Alves AJ. Beach JW. Jeong LS. Choi BG. Roey PV. Schinazi RF. Chu CK.
    J. Med. Chem.  1992,  35:  1987 
    CrossrefSuche in Google Scholar
  • 8a Danishefsky SJ. Allen JR. Angew. Chem. Int. Ed.  2000,  39:  836 
    Suche in Google Scholar
  • 8b Allen JR. Harris CR. Danishefsky SJ. J. Am. Chem. Soc.  2001,  123:  1890 
    Suche in Google Scholar
  • 9a Bird CW. Cheeseman GWH. In Comprehensive Heterocyclic Chemistry   Vol. 3:  Katritzky AK. Rees CW. Pergamon; New York: 1984.  p.1-38  
    Suche in Google Scholar
  • 9b Process Chemistry in the Pharmaceutical Industry   Gadamasetti KG. Marcel Dekker; New York: 1999. 
  • 9c Nicolaou KC. Huang X. Giuseppone N. Rao PB. Bella M. Reddy MV. Snyder SA. Angew. Chem. Int. Ed.  2001,  40:  4705 
    Suche in Google Scholar
  • 9d Ollis WD. Stanforth SP. Ramsden CA. Tetrahedron  1985,  41:  2239 
    Suche in Google Scholar
  • 10a Chou CH. Gong CL. Chao CC. Lin CH. Kwan CY. Hsieh CL. Leung YM. J. Nat. Prod.  2009,  72:  830 
    Suche in Google Scholar
  • 10b Beecham AF. Hart NK. Johns SR. Lamberton JA. Chem. Commun.  1967,  535 
  • 10c Jossang A. Jossang P. Hadi HA. Sevenet T. Bodo B. J. Org. Chem.  1991,  56:  6527 
    Suche in Google Scholar
  • 10d Miyake FY. Yakushijin K. Horne DA. Org. Lett.  2004,  6:  711 
    Suche in Google Scholar
  • 10e Miyake FY. Yakushijin K. Horne DA. Org. Lett.  2004,  6:  4249 
    Suche in Google Scholar
  • 10f Trost BM. Stiles DT. Org. Lett.  2007,  9:  2763 
    Suche in Google Scholar
  • 11 Skiles JW. McNeil D. Tetrahedron Lett.  1990,  31:  7277 
    CrossrefSuche in Google Scholar
  • 12 Grigg R. Aly MF. Sridharan V. Thianpatanagul S.
    J. Chem. Soc., Chem. Commun.  1984,  182 
  • 13a Cravotto G. Giovenzani GB. Pilati T. Sisti M. Palmisano G. J. Org. Chem.  2001,  66:  8447 
    Suche in Google Scholar
  • 13b Selvakumar N. Azhagan AM. Srinivas D. Krishna GG. Tetrahedron Lett.  2002,  43:  9175 
    Suche in Google Scholar
  • 13c Sebahar PR. Williams RM. J. Am. Chem. Soc.  2000,  122:  5666 
    Suche in Google Scholar
  • 13d Sebahar PR. Osada H. Usui T. Williams RM. Tetrahedron  2002,  58:  6311 
    Suche in Google Scholar
  • 13e Prasanna R. Purushothaman S. Raghunathan R. Tetrahedron Lett.  2010,  51:  4538 
    Suche in Google Scholar
  • 14 Kiss J. Noack K. Carbohydr. Res.  1971,  16:  245 
    CrossrefSuche in Google Scholar