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Synthesis 2011(2): 337-341  
DOI: 10.1055/s-0030-1258369
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

CeCl3˙7H2O: A Versatile and Efficient Reagent for the Synthesis of C-Pyrrolyl Glycosides

Basi V. Subba Reddy*, Ruchi Jain, Kudikyala Bhargavi, Manisha Swain, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in;
Further Information

Publication History

Received 1 November 2010
Publication Date:
17 December 2010 (online)

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Abstract

1,3-Diketones and β-oxo esters undergo smooth coupling with d-glucosamine in the presence of 25 mol% CeCl3˙7H2O in water at 80 ˚C to furnish C-pyrrolyl glycosides in good to high yields. The reaction of cyclic diketones such as dimedone with d-glucosamine affords the corresponding 2-(3,4-dihydroxytetrahydrofuran-2-yl)-6,7-dihydro-1H-indol-4(5H)-one derivatives. These dihydroxy derivatives are directly converted into acetates using acetic anhydride and 4-(dimethylamino)pyridine. The use of readily available CeCl3˙7H2O makes this procedure quite simple, convenient and practical.

Key words

C-pyrrolyl glycosides - 1,3-diones - glucosamine - cerium(III) salts

    References

  • 1 The Chemistry of Heterocyclic Compounds   Vol. 48:  Jones RA. Wiley; New York: 1990. 
  • 2a Andersen RJ. Faulkner DJ. Cun-heng H. Van Duyne GD. Clardy J. J. Am. Chem. Soc.  1985,  107:  5492 
    Search in Google Scholar
  • 2b Reddy MVR. Faulkner DJ. Venkateswarlu Y. Rao MR. Tetrahedron  1997,  53:  3457 
    Search in Google Scholar
  • For reviews, see ref. 1 and:
  • 3a Gilchrist TL. J. Chem. Soc., Perkin Trans. 1  1999,  2849 
  • 3b Boger DL. Boyce CW. Labroli MA. Sehon CA. Jin Q. J. Am. Chem. Soc.  1999,  121:  54 
    Search in Google Scholar
  • 3c Comprehensive Heterocyclic Chemistry   Vol. 2:  Bird CW. Pergamon Press; Oxford: 1996. 
  • 3d O’Hagan D. Nat. Prod. Rep.  2000,  17:  435 
    Search in Google Scholar
  • 3e Larionov OV. de Meijere A. Angew. Chem. Int. Ed.  2005,  44:  5664 ; and references cited therein
    Search in Google Scholar
  • 4a Gabriele B. Salerno G. Fazio A. J. Org. Chem.  2003,  68:  7853 ; and references cited therein
    Search in Google Scholar
  • 4b Furstner A. Angew. Chem. Int. Ed.  2003,  42:  3582 
    Search in Google Scholar
  • 4c Jacobi PA. Coults LD. Guo JS. Leung SI. J. Org. Chem.  2000,  65:  205 
    Search in Google Scholar
  • 4d Fumoto Y. Eguchi T. Uno H. Ono N.
    J. Org. Chem.  1999,  64:  6518 
    Search in Google Scholar
  • 4e Dannhardt G. Kiefer W. Kraemer G. Maehrlein S. Nowe U. Fiebich B. Eur. J. Med. Chem.  2000,  35:  499 
    Search in Google Scholar
  • 4f Ragno R. Marshall GR. Santo RD. Costi R. Massa S. Rompei R. Artico M. Bioorg. Med. Chem.  2000,  8:  1423 
    Search in Google Scholar
  • 5a Thompson RB. FASEB J.  2001,  15:  1671 
    Search in Google Scholar
  • 5b Muchowski JM. Adv. Med. Chem.  1992,  1:  109 
    Search in Google Scholar
  • 5c Cozzi P. Mongelli N. Curr. Pharm. Des.  1998,  4:  181 
    Search in Google Scholar
  • 5d Furstner A. Szillat H. Gabor B. Mynott R. J. Am. Chem. Soc.  1998,  120:  8305 
    Search in Google Scholar
  • 6a Baumgarten M. Tyulyulkor N. Chem. Eur. J.  1998,  4:  987 
    Search in Google Scholar
  • 6b Lee C.-F. Yang L.-M. Hwu T.-Y. Feng A.-S. Tseng J.-C. Luh T.-Y. J. Am. Chem. Soc.  2000,  122:  4992 
    Search in Google Scholar
  • 6c Groenendaal L. Meijer EW. Vekemans JAJM. In Electronic Materials: The Oligomer Approach   Müllen K. Wegner G. Wiley-VCH; Weinheim: Germany: 1997. 
  • 6d Domingo VM. Aleman C. Brillas F. Julia L. J. Org. Chem.  2001,  66:  4058 
    Search in Google Scholar
  • 7a Handbook of Conducting Polymers   2nd ed.:  Skotheim TA. Elsenbaumer RL. Reynolds JR. Marcel Dekker; New York: 1998. 
  • 7b Higgins S. Chem. Soc. Rev.  1997,  26:  247 
    Search in Google Scholar
  • 8a Prins LJ. Reinhoudt DN. Timmerman P. Angew. Chem. Int. Ed.  2001,  40:  2382 
    Search in Google Scholar
  • 8b Lehn JM. Supramolecular Chemistry, Concepts and Perspectives   VCH; Weinheim: Germany: 1995. 
  • 9a Gale PA. Anzenbacher P. Sessler JL. Coord. Chem. Rev.  2001,  222:  57 
    Search in Google Scholar
  • 9b Vicente MGH. Jaquinod L. Smith KM. Chem. Commun.  1999,  1771 
  • 9c Yoon DW. Hwang H. Lee C.-H. Angew. Chem. Int. Ed.  2002,  41:  1757 
    Search in Google Scholar
  • 9d Jeppesen JO. Becher J. Eur. J. Org. Chem.  2003,  3245 
  • 9e Miyaji H. Sato W. Sessler JL. Angew. Chem. Int. Ed.  2000,  39:  1777 
    Search in Google Scholar
  • 9f Montforts FP. Kutzki O. Angew. Chem. Int. Ed.  2000,  39:  599 
    Search in Google Scholar
  • 10a Ferreira VF. Desouza MCBV. Cunha AC. Pereira LOR. Ferreira MLG. Org. Prep. Proced. Int.  2001,  33:  411 
    Search in Google Scholar
  • 10b Zeng DX. Chen Y. Synlett  2006,  490 ; and references cited therein
  • 10c Tracey MR. Husung RP. Lambeth RH. Synthesis  2004,  918 ; and references cited therein
  • 10d Song C. Knight DW. Whatton MA. Org. Lett.  2006,  8:  163 
    Search in Google Scholar
  • 11a Sánchez AG. Toledano E. Guillén MG. J. Chem. Soc., Perkin Trans. 1  1974,  1237 
  • 11b Yadav JS. Reddy BVS. Srinivas M. Satheesh G. Synthesis  2007,  1712 
  • 12 Yadav JS. Reddy BVS. Srinivas M. Divyavani C. Basha SJ. Sarma AVS. J. Org. Chem.  2008,  73:  3252 
    CrossrefSearch in Google Scholar
  • 13a Grieco PA. Organic Synthesis in Water   Blackie Academic & Professional; London: 1998. 
  • 13b Li CJ. Chan TH. Organic Reactions in Aqueous Media   John Wiley & Sons; New York: 1997.  p.159