Download PDF
Synthesis 2009(19): 3285-3292  
DOI: 10.1055/s-0029-1216953
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of (+)-Dodoneine and Its 6-Epimer

Gowravaram Sabitha*, Vangala Bhaskar, S. Siva Sankara Reddy, Jhillu S. Yadav
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com;
Further Information

Publication History

Received 20 March 2009
Publication Date:
21 August 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

The total synthesis of dodoneine and its 6-epimer is described­, using HKR of epoxide and reduction with SmI2 reactions as key steps, respectively.

Key words

dodoneine - epidodoneine - trimethylsulfonium iodide - HKR - SmI2 - RCM

    References

  • 1 Ouedragogo M. Carreyre H. Vandebrouck C. Bescond J. Raymond G. Guissou I.-P. Cognard C. Becq F. Potreau D. Cousson A. Marrot J. Coustard J.-M. J. Nat. Prod.  2007,  70:  2006 
    CrossrefGoogle Scholar
  • 2a Robert R. Thoreau V. Norez C. Cantereau A. Mettey Y. Rogier C. Becq F. J. Biol. Chem.  2004,  279:  21160 
    Google Scholar
  • 2b Vandebrouck C. Melin P. Norez C. Robert R. Guibert C. Mettey Y. Becq F. Respir. Res.  2006,  7:  113 
    Google Scholar
  • 3a Bercedo PA. Falomir E. Murga J. Carda M. Marco JA. Eur. J. Org. Chem.  2008,  4015 
    Google Scholar
  • 3b Srihari P. Rajendar G. Rao RS. Yadav JS. Tetrahedron Lett.  2008,  49:  5590 
    Google Scholar
  • 3c Dittoo A. Bellosta V. Cooy J. Synlett  2008,  2459 
    Google Scholar
  • 4a Sabitha G. Sudhakar K. Reddy NM. Rajkumar M. Yadav JS. Tetrahedron Lett.  2005,  46:  6567 
    Google Scholar
  • 4b Sabitha G. Narjis F. Swapna R. Yadav JS. Synthesis  2006,  2879 
    Google Scholar
  • 4c Sabitha G. Reddy EV. Yadagiri K. Yadav JS. Synthesis  2006,  3270 
    Google Scholar
  • 4d Sabitha G. Sudhakar K. Yadav JS. Tetrahedron Lett.  2006,  47:  8599 
    Google Scholar
  • 4e Sabitha G. Bhaskar V. Yadav JS. Tetrahedron Lett.  2006,  47:  8179 
    Google Scholar
  • 4f Sabitha G. Swapna R. Reddy EV. Yadav JS. Synthesis  2006,  4242 
    Google Scholar
  • 4g Sabitha G. Bhikshapathi M. Yadav JS. Synth. Commun.  2007,  37:  561 
    Google Scholar
  • 4h Sabitha G. Gopal P. Yadav JS. Synth. Commun.  2007,  37:  1495 
    Google Scholar
  • 4i Sabitha G. Yadagiri K. Yadav JS. Tetrahedron Lett.  2007,  48:  1651 
    Google Scholar
  • 4j Sabitha G. Gopal P. Reddy CN. Yadav JS. Tetrahedron: Asymmetry  2009,  20:  184 
    Google Scholar
  • 5 Lescure P. Huet F. Synthesis  1987,  404 
    Article in Thieme ConnectGoogle Scholar
  • 6a Schaus SE. Brandes BD. Larrow JF. Tokunaga M. Hansen KB. Gould AE. Furrow ME. Jacobsen EN. J. Am. Chem. Soc.  2002,  124:  1307 
    Google Scholar
  • 6b Louis JT. Nelson WL. J. Org. Chem.  1987,  52:  1309 
    Google Scholar
  • 7 Rychnovsky SD. Rogers BN. Richardson RI. Acc. Chem. Res.  1998,  31:  9 
    CrossrefGoogle Scholar
  • 8a Fürstner A. Angew. Chem. Int. Ed.  2000,  39:  3012 
    Google Scholar
  • 8b Tanaka TM. Grubbs RH. Acc. Chem. Res.  2001,  34:  18 
    Google Scholar
  • 8c Grubbs RH. Tetrahedron  2004,  44:  2449 
    Google Scholar
  • 8d Grubbs RH. Tetrahedron  2004,  60:  7117 
    Google Scholar
  • 8e Love JA. In Handbook of Metathesis   Vol. 2:  Grubbs RH. Wiley-VCH; Weinheim: 2003.  p.296-322  
    Google Scholar
  • 9 Evans DA. Gauchet-Prunet JA. J. Org. Chem.  1993,  58:  2446 
    CrossrefGoogle Scholar
  • 10a Petrier C. Luche JL. J. Org. Chem.  1985,  50:  910 
    Google Scholar
  • 10b Einhorn C. Luche JL. J. Organomet. Chem.  1987,  322:  177 
    Google Scholar
  • 10c Chattopadhyay A. J. Org. Chem.  1996,  61:  6104 
    Google Scholar
  • 11 Dess PB. Martin JC. J. Am. Chem. Soc.  1978,  100:  300 
    CrossrefGoogle Scholar
  • 12a Keck GE. Wager CA. Org. Lett.  2000,  2:  2307 
    Google Scholar
  • 12b Keck GE. Wager CA. Sell T. Wager T. S. J. Org. Chem.  1999,  64:  2172 
    Google Scholar