Synthesis 2001(12): 1846-1850
DOI: 10.1055/s-2001-17513
PAPER
© Georg Thieme Verlag Stuttgart · New York

Iodine Mediated Lactonization of Terpenic 3-Hydroxy Acids

Tsutomu Fujita*b,, Naoto Hanyua, Takashi Minob, Masami Sakamotoa
a Graduate School of Science and Technology, Chiba University, 1-33, Yayoicho, Inage-ku, Chiba, Japan 263-8522
b Department of Materials Technology, Faculty of Engineering, Chiba University, 1-33, Yayoicho, Inage-ku, Chiba, Japan 263-8522
Fax: +81(43)2903386; e-Mail: fuji@planet.tc.chiba-u.ac.jp;
Further Information

Publication History

Received 1 March 2001
Publication Date:
11 August 2004 (online)

Abstract

Cyclization of terpenic 3-hydroxy acids in the presence of a catalytic amount of iodine gave bicyclic or tricyclic lactones in good yield.

    References

  • 1a Harding KE. Tiner TH. Comprehensive Organic Synthesis   Vol. 4:  Trost BM. Pergamon Press; New York: 1991.  p.363-421  
  • 1b Cardillo G. Orena M. Tetrahedron  1990,  46:  3321 
  • 1c Dowle MD. Davies DI. Chem. Soc. Rev.  1979,  8:  171 
  • 2 Kim KM. Ryu EK. Tetrahedron Lett.  1996,  37:  1441 
  • 3a Fujita T. Suga K. Watanabe S. Yanagi R. J. Appl. Chem. Biotechnol.  1977,  27:  593 
  • 3b Fujita T. Watanabe S. Suga K. Yanagi R. Tsukagoshi F. J. Org. Chem.  1978,  43:  1248 
  • 3c Fujita T. Watanabe S. Suga K. Kuramochi T. Tsukagoshi F. J. Chem. Technol. Biotechnol.  1979,  29:  31 
  • 3d Fujita T. Watanabe S. Suga K. Saita M. Sugahara K. J. Chem. Technol. Biotechnol.  1982,  32:  421 
  • 3e Fujita T. Watanabe S. Suga K. Higuchi Y. Sotoguchi T. J. Org. Chem.  1984,  49:  1975 
  • 3f Fujita T. Watanabe S. Miharu K. Itoh K. Sugahara K. J. Chem. Technol. Biotechnol.  1985,  35A:  57 
  • 3g Fujita T. Watanabe S. Sotoguchi T. Ogawa K. Sugahara K. Aust. J. Chem.  1986,  39:  799 
  • 4a Hanyu N. Mino T. Sakamoto M. Fujita T. Tetrahedron Lett.  2000,  21:  4587 
  • 4b Hanyu N. Aoki T. Mino T. Sakamoto M. Fujita T. Tetrahedron: Asymmetry  2000,  11:  4127 
  • 5a Wagner R. J. Russ. Phys. Chem. Soc.  1899,  31:  690 
  • 5b Meerwein H. Liebigs Ann.Chem.  1914,  405:  129