Download PDF
Synthesis 2010(24): 4307-4311  
DOI: 10.1055/s-0030-1258315
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Studies on Callipeltin A: Stereoselective Synthesis of (2R,3R,4S)-3-Hydroxy-2,4,6-trimethylheptanoic Acid

Gowravaram Sabitha*, K. Yadagiri, G. Chandrashekhar, J. S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
Further Information

Publication History

Received 6 September 2010
Publication Date:
22 October 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

Asymmetric synthesis of (2R,3R,4S)-3-hydroxy-2,4,6-trimethylheptanoic acid, the β-hydroxy acid unit that acylates the N-terminus of cyclic depsipeptide callipeltin A, has been devised. The approach involves the desymmetrization of a bicyclic precursor, which generates the three chiral centers.

Key words

asymmetric synthesis - callipeltin A - desymmetrization - natural products

    References

  • 1 Zampella A. Sepe V. Luciano P. Bellotta F. Monti MC. Auria MVD. Jepsen T. Petek S. Adeline MT. Laprevote O. Aubertin AM. Debitus C. Poupat C. Ahond A. J. Org. Chem.  2008,  73:  5319 
    CrossrefGoogle Scholar
  • 2 Oku N. Gustafson KR. Cartner LK. Wilson JA. Shigematsu N. Hess S. Pannell LK. Boyd MR. McMahon JB. J. Nat. Prod.  2004,  67:  1407 
    CrossrefGoogle Scholar
  • 3 Ford PW. Gustafson KR. McKee TC. Shigematsu N. Maurizi LK. Pannell LK. Williams DE. De Silva ED. Lassota P. Allen TM. Soest RV. Andersen RJ. Boyd MR. J. Am. Chem. Soc.  1999,  121:  5899 
    CrossrefGoogle Scholar
  • 4 Ratnayake AS. Bugni TS. Feng X. Harper MK. Skalicky JJ. Mohammed KA. Andjelic CD. Barrows LR. Ireland CM. J. Nat. Prod.  2006,  69:  1582 
    CrossrefGoogle Scholar
  • 5 Plaza A. Gustchina E. Baker HL. Kelly M. Bewley C. J. Nat. Prod.  2004,  70:  1753 
    CrossrefGoogle Scholar
  • 6a Zampella A. D’Auria MV. Gomez Paloma L. Casapullo A. Minale L. Debitus C. Henin Y. J. Am. Chem. Soc.  1996,  118:  6202 
    Google Scholar
  • 6b D’Auria MV. Zampella A. Gomez Paloma L. Casapullo A. Minale L. Debitus C. Roussakis C. Bert VL. Tetrahedron  1996,  52:  9589 
    Google Scholar
  • 7 Trevisi L. Bova S. Cargnelli G. Danieli-Betto D. Floreani M. Germinario E. D’Auria MV. Luciani S. Biochem. Biophys. Res. Commun.  2000,  279:  219 
    CrossrefGoogle Scholar
  • 8 Guerlavais V. Carroll PJ. Joullié MM. Tetrahedron: Asymmetry  2002,  13:  675 
    CrossrefGoogle Scholar
  • 9a Yadav JS. Rao CS. Chandrashekar S. Ramarao AV. Tetrahedron Lett.  1995,  36:  7717 
    Google Scholar
  • 9b Yadav JS. Abraham S. Reddy MM. Sabitha G. Sankar AR. Kunwar AC. Tetrahedron Lett.  2001,  42:  4713 
    Google Scholar
  • 9c Yadav JS. Bhaskar Reddy K. Sabitha G. Tetrahedron  2008,  64:  1971 
    Google Scholar
  • 10 Sire BQ. Zard SZ. Tetrahedron Lett.  1995,  36:  7717 
    CrossrefGoogle Scholar
  • 11 Bal BS. Childers WE. Pinnick HW. Tetrahedron  1981,  37:  2091 
    CrossrefGoogle Scholar