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Synlett 2011(2): 215-218  
DOI: 10.1055/s-0030-1259302
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular [4+2]-Cycloaddition of 5-Amino-Substituted Oxazoles as an Approach toward the Left-Hand Segment of Haplophytine

Majid Chughtai, James M. Eagan, Albert Padwa*
Department of Chemistry, Emory University, Atlanta, GA 30322, USA
Fax: +1(404)7276629; e-Mail: chemap@emory.edu;
Further Information

Publication History

Received 30 August 2010
Publication Date:
05 January 2011 (online)

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Abstract

The [4+2]-cycloaddition chemistry of several 5-amino-substituted oxazoles has been examined as an approach toward the construction of the left-half segment of the aspidosperma alkaloid haplophytine.

Key words

5-aminooxazoles - intramolecular - Diels-Alder reaction - pyridines - haplophytine

    References

  • 1a Weinreb SM. Chem. Rev.  2006,  106:  2531 
    Google Scholar
  • 1b Jeong JH. Weinreb SM. Org. Lett.  2006,  8:  2309 
    Google Scholar
  • 2a Weingarten MD. Prein M. Price AT. Snyder JP. Padwa A. J. Org. Chem.  1997,  62:  2001 
    Google Scholar
  • 2b Padwa A. Lynch SM. Mejiá-Oneto JM. Zhang H. J. Org. Chem.  2005,  70:  2206 
    Google Scholar
  • 2c Meijá-Oneto JM. Padwa A. Tetrahedron Lett.  2004,  45:  9115 
    Google Scholar
  • 3a Padwa A. Dimitroff M. Waterson AG. Wu T. J. Org. Chem.  1997,  62:  4088 
    Google Scholar
  • 3b Padwa A. Wang Q.
    J. Org. Chem.  2006,  71:  7391 
    Google Scholar
  • 3c Zhang H. Padwa A. Org. Lett.  2006,  8:  247 
    Google Scholar
  • 3d Zhang H. Boonsombat J. Padwa A. Org. Lett.  2007,  9:  279 
    Google Scholar
  • 4a Mejiá-Oneto JM. Padwa A. Org. Lett.  2004,  6:  3241 
    Google Scholar
  • 4b Padwa A. Lynch SM. Mejiá-Oneto JM. Zhang H. J. Org. Chem.  2005,  70:  2206 
    Google Scholar
  • 4c Irgolic KJ. In Houben-Weyl   4th ed., Vol. E12b:  Klamann D. Thieme; Stuttgart: 1990.  p.150 
    Google Scholar
  • 5 Saxton JE. in The Aldaloids: Chemistry and Biology   Vol. 51:  Cordell GA. Academic Press; San Diego / CA: 1998.  p.1-197  
    CrossrefGoogle Scholar
  • 6 Yates P. MacLachlan FN. Rae ID. Rosenberger M. Szabo AG. Willis CR. Cava MP. Behforouz M. Lakshimikantham MV. Ziegler W. J. Am. Chem. Soc.  1973,  95:  7842 
    CrossrefGoogle Scholar
  • 7a He F. Bo Y. Altom JD. Corey EJ. J. Am. Chem. Soc.  1999,  121:  6771 
    Google Scholar
  • 7b Sumi S. Matsumoto K. Tokuyama H. Fukuyama T. Org. Lett.  2003,  5:  1891 
    Google Scholar
  • 7c Sumi S. Matsumoto K. Tokuyama H. Fukuyama T. Tetrahedron  2003,  59:  8571 
    Google Scholar
  • 7d Marino JP. Cao G. Tetrahedron Lett.  2006,  47:  7711 
    Google Scholar
  • 7e Nicolaou KC. Dalby SM. Majumder U. J. Am. Chem. Soc.  2008,  130:  14942 
    Google Scholar
  • 8 Mejiá-Oneto JM. Padwa A. Org. Lett.  2006,  8:  3275 
    CrossrefGoogle Scholar
  • 9 Ueda H. Satoh H. Matsumoto K. Sugimoto K. Fukuyama T. Tokuyama H. Angew Chem. Int. Ed.  2009,  48:  7736 
    CrossrefGoogle Scholar
  • 10 Nicolaou KC. Dalby SM. Li S. Suzuki T. Chen DY.-K. Angew Chem. Int. Ed.  2009,  48:  7616 
    CrossrefGoogle Scholar
  • 11a Matsumoto K. Tokuyama H. Fukyama T. Synlett  2007,  3137 
    Google Scholar
  • 11b Nicolaou KC. Majumder U. Roche SP. Chen DY.-K. Angew Chem. Int. Ed.  2007,  46:  4715 
    Google Scholar
  • 12 For a review on bimolecular oxazole Diels-Alder reactions, see: Levin JI. Laakso LM. The Chemistry of Heterocyclic Compounds   Vol. 60, Part A:  Palmer DC. John Wiley and Sons; Hoboken / NJ: 2003.  p.417-472  
    CrossrefGoogle Scholar
  • 13a Kondratèva GY. Khim. Nauka Prom.  1957,  2:  666 ; Chem. Abstr. 1958, 52, 6345a
    Google Scholar
  • 13b Kondratèva GY. Izv. Akad. Nauk SSSR., Otd. Khim. Nauk  1959,  484 ; Chem. Abstr. 1959, 53, 21940d
    Google Scholar
  • For some leading references, see:
  • 14a Jacobi PA. Advances in Heterocyclic Natural Product Synthesis   Vol. 2:  Pearson WH. JAI Press; Greenwich / CT: 1992.  p.251-299  
    Google Scholar
  • 14b Levin JI. Weinreb SM. J. Am. Chem. Soc.  1983,  105:  1397 
    Google Scholar
  • 14c Levin JI. Weinreb SM. J. Org. Chem.  1984,  49:  4325 
    Google Scholar
  • 14d Subramanyam C. Noguchi M. Weinreb SM. J. Org. Chem.  1989,  54:  5580 
    Google Scholar
  • For some examples of intramolecular oxazole-olefin Diels-Alder reactions, see:
  • 15a Shimada S. Tojo T. Chem. Pharm. Bull.  1983,  31:  4247 
    Google Scholar
  • 15b Levin JI. Tetrahedron Lett.  1989,  30:  2355 
    Google Scholar
  • 15c Subramanyam C. Noguchi M. Weinreb SM. J. Org. Chem.  1989,  54:  5580 
    Google Scholar
  • 15d Jung ME. Dansereau SMK. Heterocycles  1994,  39:  767 
    Google Scholar
  • 15e Padwa A. Brodney MA. Liu B. Satake K. Wu T. J. Org. Chem.  1999,  64:  3595 
    Google Scholar
  • 15f Sun X. Janvier P. Zhao G. Bienaymé H. Zhu J. Org. Lett.  2001,  3:  877 
    Google Scholar
  • 15g Janvier P. Sun X. Bienaymé H. Zhu J. J. Am. Chem. Soc.  2002,  124:  2560 
    Google Scholar
  • 15h González-Zamora E. Fayol A. Bois-Choussy M. Chiaroni A. Zhu J. Chem. Commun.  2001,  1684 
    Google Scholar
  • 15i Gámez-Montano R. González-Zamora E. Potier P. Zhu J. Tetrahedron  2002,  58:  6351 
    Google Scholar
  • 16a Clerin D. Kille G. Fleury JP. Tetrahedron  1974,  30:  469 
    Google Scholar
  • 16b Clerin D. Fleury JP. Bull. Soc. Chim. Fr.  1973,  3127 
    Google Scholar
  • 17 Lipshutz BH. Hungate RW. McCarthy KE. J. Am. Chem. Soc.  1983,  105:  7703 
    CrossrefGoogle Scholar