Download PDF
Synthesis 2011(4): 549-552  
DOI: 10.1055/s-0030-1258413
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

A Modular Synthesis of Fluorinated, Chiral Polar Lipids

Christoph Bucher, Ryan Gilmour*
Laboratory for Organic Chemistry, ETH Zurich, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland
Fax: +41(44)6331235; e-Mail: ryan.gilmour@org.chem.ethz.ch;
Further Information

Publication History

Received 2 December 2010
Publication Date:
19 January 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

The synthesis of a small collection of chiral, polar lipids is described starting from (S)-solketal and epichlorohydrin.

Key words

amphipathic - β-fluoroamines - coupling - fluorine - lipid - synthesis

    References

  • 1a Li S. Huang L. Gene Therapy  2000,  7:  31 
    Google Scholar
  • 1b Cavazzana-Calvo M. Thrasher A. Mavilio F. Nature  2004,  427:  779 
    Google Scholar
  • 1c Hoag H. Nature  2005,  435:  530 
    Google Scholar
  • 2a Miller AD. Angew. Chem. Int. Ed.  1998,  37:  1768 
    Google Scholar
  • 2b Elsabahy M. Wazen N. Bayo-Puxan N. Deleavey G. Servant M. Damha M. Leroux JC. Adv. Funct. Mater.  2009,  19:  3862 
    Google Scholar
  • 2c Zhu L. Mahato RI. Expert Opin. Drug. Deliv.  2010,  7:  1209 
    Google Scholar
  • 3a Sparr C. Schweizer WB. Senn HM. Gilmour R. Angew. Chem. Int. Ed.  2009,  48:  3065 
    Google Scholar
  • 3b Bucher C. Sparr C. Schweizer WB. Gilmour R. Chem. Eur. J.  2009,  15:  7637 
    Google Scholar
  • 3c Sparr C. Tanzer E.-M. Bachmann J. Gilmour R. Synthesis  2010,  1394 
    Google Scholar
  • 3d Bucher C. Mondelli C. Baiker A. Gilmour R. J. Mol. Catal. A: Chem.  2010,  327:  87 
    Google Scholar
  • 3e Sparr C. Gilmour R. Angew. Chem. Int. Ed.  2010,  49:  6520 
    Google Scholar
  • 3f Bucher C. Gilmour R. Angew. Chem. Int. Ed.  2010,  49:  8724 
    Google Scholar
  • 3g Paul S. Schweizer WB. Ebert M.-O. Gilmour R. Organometallics  2010,  29:  4424 
    Google Scholar
  • 5 Smart BE. J. Fluorine Chem.  2001,  109:  3 
    CrossrefGoogle Scholar
  • 6 Hodges JA. Raines RT. J. Am. Chem. Soc.  2003,  125:  9262 
    CrossrefGoogle Scholar
  • For examples of related reactions see
  • 7a Lemaire M. Jeminet G. Gourcy J.-G. Dauphin G. Tetrahedron: Asymmetry  1993,  4:  2101 
    Google Scholar
  • 7b Cassel S. Debaig C. Benvegnu T. Chaimbault P. Lafosse M. Plusquellec D. Rollin P. Eur. J. Org. Chem.  2001,  875 
    Google Scholar
  • 7c Kawagishi T. Yoshikawa K. Ubukata M. Hamada M. Nakajima N. Heterocycles  2006,  69:  107 
    Google Scholar
4

(+)-(S)-Solketal is available from a number of suppliers including TCI-Deutschland [25 g = 364.36 CHF]. Epichlorohydrin(racemic) was purchased from Sigma-Aldrich [100 g = 39.76 CHF].

8

Both cis-4-fluoroproline [1 g = 380.77 CHF] and trans-4-fluoroproline [1 g = 559.93 CHF] are commercially available from Bachem.