Synthesis 2009(5): 864-867  
DOI: 10.1055/s-0028-1083364
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Baker’s Yeast for Sweet Dough Enables Large-Scale Synthesis of Enantiomerically Pure Bicyclo[3.3.1]nonane-2,6-dione

Carl Johan Wallentina, Edvinas Orentasb, Eugenijus Butkusb, Kenneth Wärnmark*a
a Organic Chemistry, Department of Chemistry, Lund University, P.O. Box 124, 22100 Lund, Sweden
Fax: +46(46)2228209; e-Mail: [email protected];
b Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius, Lithuania
Fax: +370(5)92330987; e-Mail: [email protected];
Further Information

Publication History

Received 22 August 2008
Publication Date:
11 February 2009 (online)

Abstract

An improved synthetic procedure of racemic bicyclo[3.3.1]nonane-2,6-dione has been developed. Employing Baker’s yeast for sweet dough made it possible to kinetically resolve the racemic compound and to isolate enantiomerically pure (+)-bicyclo[3.3.1]nonane-2,6-dione on a large scale. Furthermore, the developed procedure made it possible to produce (-)-bicyclo[3.3.1]nonane-2,6-dione with an enantiomeric excess of 75%.

    References

  • 1 Butkus E. Synlett  2001,  1827 
  • 2 Feng S. Xia Y. Han D. Zheng C. He X. Tang X. Bai D. Bioorg. Med. Chem. Lett.  2005,  15:  523 
  • 3 Usuda H. Kanai M. Shibasaki M. Tetrahedron Lett.  2002,  43:  3621 
  • 4 Spessard SJ. Stoltz BM. Org. Lett.  2002,  4:  1943 
  • 5 Otomaru Y. Kina A. Shintani R. Hayashi T. Tetrahedron: Asymmetry  2005,  16:  1673 
  • 6 Graetz B. Rychnovsky S. Leu W.-H. Farmer P. Lin R. Tetrahedron: Asymmetry  2005,  16:  3584 
  • 7 Grossman RB. Tsai J.-C. Davis WM. Gutierrez A. Buchwald SL. Organometallics  1994,  13:  3892 
  • 8 Orentas E. Bagd˛iunas G. Berg U. ilinskas A. Butkus E. Eur. J. Org. Chem.  2007,  4251 
  • 9 ilinskas A. Stončius S. Butkus E. Chirality  2005,  17:  S70 
  • 10 Butkus E. ilinskas A. Stončius S. Rozenbergas R. Urbanová M. Setnička V. Bour P. Volka K. Tetrahedron: Asymmetry  2002,  13:  633 
  • 11 Butkus E. Berg U. ilinskas A. Kubilius R. Stončius S. Tetrahedron: Asymmetry  2000,  11:  3053 
  • 12 Butkus E. Berg U. Malinauskiene J. Sandström J. J. Org. Chem.  2000,  65:  1353 
  • 13 Naemura K. Matsumura T. Komatsu M. Hirose Y. Chikamatsu H. Bull. Chem. Soc. Jpn.  1989,  62:  3523 
  • 14 Naemura K. Matsumura T. Komatsu M. Hirose Y. Chikamatsu H. J. Chem. Soc., Chem. Commun.  1988,  239 
  • 15 Stončius S. Orentas E. Butkus E. Öhrström L. Wendt OF. Wärnmark K. J. Am. Chem. Soc.  2006,  128:  8272 
  • 16 Stončius S. Butkus E. ilinskas A. Larsson K. Öhrström L. Berg U. Wärnmark K. J. Org. Chem.  2004,  69:  5196 
  • 17 Marjo C. Bishop R. Eur. J. Org. Chem.  2001,  863 
  • 18 Butkus E. Berg U. J. Chem. Res., Synop.  1993,  116 
  • 19 Mitsuo M. Masahiro N. Shigeaki O. Osamu M. Genzoh T. Hiromu K. J. Chem. Technol. Biotechnol.  1998,  281 
  • 20 Naemura K. Ida H. Fukuda R. Bull. Chem. Soc. Jpn.  1993,  66:  573 
  • 21 Snatzke G. Wolfram B. Tetrahedron  1972,  28:  655 
  • 22 Gerlach H. Helv. Chim. Acta  1978,  61:  2773 
  • 23 Hoffmann G. Wiartalla R. Tetrahedron Lett.  1982,  23:  3887 
  • 24 Meerwein H. Schurmann W. Justus Liebigs Ann. Chem.  1913,  398:  196 
  • 25 Schaefer JP. Honig LM. J. Org. Chem.  1968,  33:  2655 
  • 26 Quast H. Witzel M. Liebigs Ann. Chem.  1993,  699 
  • 27 Lightner DA. Chang TC. Hefelfinger DT. Jackman DE. Wijekoon WMD. Givens JW. J. Am. Chem. Soc.  1985,  107:  7499 
  • 28 Mislin G. Miesch M. Eur. J. Org. Chem.  2001,  1753 
  • 29 Peters JA. Synthesis  1979,  321 
  • 30 Henkel JG. Faith WC. Hane JT. J. Org. Chem.  1981,  46:  3483 
  • 31 Mayr M. Bataille CJR. Gosiewska S. Raskatov JA. Brown JM. Tetrahedron: Asymmetry  2008,  19:  1328 
  • 32 Steven VL. Joanne N. William PG. Stephen PM. Synthesis  1994,  639 
  • 34 Stephens PJ. McCann DM. Butkus E. Stončius S. Cheeseman JR. Frisch MJ. J. Org. Chem.  2004,  69:  1948 
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Jästbolaget AB, P. O. Box 7003, 192 07 Sollentuna, Sweden.

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Ketol 3 can be collected as a nearly 1:1 mixture of the endo- and exo-isomers in the second fraction in the chromato-graphic purification of (+)-1 by eluting with EtOAc.