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Synthesis 2012(1): 83-86  
DOI: 10.1055/s-0031-1289634
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

(N-tert-Butanesulfinyl)imines in Alkaloid Synthesis: Concise Formal Syntheses of the Dendrobate Alkaloid (+)-241D and Its C-4 Epimer [¹]

Kongara Damodar, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;
Further Information

Publication History

Received 17 August 2011
Publication Date:
02 December 2011 (online)

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Abstract

Concise formal syntheses of the dendrobate alkaloid (+)-241D and its C-4 epimer are described by means of a highly diastereoselective Barbier-type indium-mediated allylation strategy involving an (S)-(N-tert-butanesulfinyl)imine.

Key words

(N-tert-butanesulfinyl)imine - piperidine alkaloids - aldol reaction - alkaloid-241D - allylation

1

Part 50 in the series ‘Synthetic studies on natural products’.

    References

  • 2b Liu G. Cogan DA. Ellman JA. J. Am. Chem. Soc.  1997,  119:  9913 
    Google Scholar
  • 3a Strunz GM. Findlay JA. In The Alkaloids   Vol. 26:  Brossi A. Academic Press; San Diego: 1986.  p.89 
    Google Scholar
  • 3b Schneider MJ. In Alkaloids: Chemical and Biological Perspectives   Vol. 10:  Pelletier SW. Pergamon; Oxford: 1996.  p.155-299  
    Google Scholar
  • 3c Fodor GB. Colasanti B. In Alkaloids: Chemical and Biological Properties   Vol. 3:  Pelletier SW. Wiley; New York: 1986.  p.1 
    Google Scholar
  • 4 Watson PS. Jiang B. Scott B. Org. Lett.  2000,  2:  3679 
    Google Scholar
  • 5a Blum MS. Jones TH. Fales HS. Tetrahedron  1982,  38:  1949 
    Google Scholar
  • 5b Leclerq S. Thirionet I. Broeders F. Daloze D. Vander Meer R. Braeckman JC. Tetrahedron  1994,  50:  8465 
    Google Scholar
  • 6a Kotha S. Deb AC. Lahiri K. Manivannan E. Synthesis  2009,  165 
    Google Scholar
  • 6b Trost BM. Brennan MK. Synthesis  2009,  3003 
    Google Scholar
  • 6c Ranaivondrambola T. Hatton W. Felpin F.-X. Evain M. Mathe-Allainmat M. Labreton J. Synlett  2010,  1631 
    Google Scholar
  • 6d Rinner U. Lentsch C. Aichinger C. Synthesis  2010,  3763 
    Google Scholar
  • 7 Daly JW. Garraffo HM. Spande TF. Amphibian Alkaloids, In The Alkaloids   Vol. 43:  Cordell GA. Academic Press; New York: 1993.  p.185 
    Google Scholar
  • 8 Daly JW. Myers CW. Whittaker N. Toxicon  1987,  25:  1023 
    Google Scholar
  • 9a Edwards MW. Garraffo HM. Daly JW. Synthesis  1994,  1167 
    Google Scholar
  • 9b Chenevert R. Dickmann M. J. Org. Chem.  1996,  61:  3332 
    Google Scholar
  • 9c Ciblat S. Calinaud P. Canet J.-L. Troin Y. J. Chem. Soc., Perkin Trans. 1  2000,  353 
    Google Scholar
  • 9d Ma D. Sun H. Org. Lett.  2000,  2:  2503 
    Google Scholar
  • 9e Davis FA. Chao B. Rao A. Org. Lett.  2001,  3:  3169 
    Google Scholar
  • 9f Monfray J. Gelas-Mialhe Y. Gramain J.-C. Remuson R. Tetrahedron: Asymmetry  2005,  16:  1025 
    Google Scholar
  • 9g Gnamm C. Krauter CM. Brodner K. Helmchen G. Chem. Eur. J.  2009,  15:  2050 
    Google Scholar
  • 9h Girard N. Hurvois J.-P. Tetrahedron Lett.  2007,  48:  4097 
    Google Scholar
  • 9i Kumar RSC. Reddy GV. Shankaraiah G. Babu KS. Rao JM. Tetrahedron Lett.  2010,  51:  1114 
    Google Scholar
  • 10 Robak MT. Herbage MA. Ellman JA. Chem. Rev.  2010,  110:  3600 
    Google Scholar
  • 11a Damodar K. Lingaiah M. Nisith B. Das B. Synthesis  2011,  2478 
    Google Scholar
  • 11b Das B. Satyalakshmi G. Suneel K. Synthesis  2011,  2437 
    Google Scholar
  • 11c Das B. Kumar DN. Synlett  2011,  1285 
    Google Scholar
  • 12a Cogan DA. Ellman JA. J. Am. Chem. Soc.  1999,  121:  268 
    Google Scholar
  • 12b Liu G. Cogan DA. Owens TD. Tang TP. Ellman JA. J. Org. Chem.  1999,  64:  1278 
    Google Scholar
  • 13 Foubelo F. Yus M. Tetrahedron: Asymmetry  2004,  15:  3823 
    Google Scholar
  • 14 Lou S. Moquist PN. Schaus SE. J. Am. Chem. Soc.  2007,  129:  15398 
    Google Scholar
  • 15 Raymond J.-L. Chen Y. J. Org. Chem.  1995,  60:  6970 
    Google Scholar
1

Part 50 in the series ‘Synthetic studies on natural products’.