Elsevier

Tetrahedron Letters

Volume 51, Issue 6, 10 February 2010, Pages 983-986
Tetrahedron Letters

Improved synthesis of 1,5-dinaphtho[38]crown-10

https://doi.org/10.1016/j.tetlet.2009.12.060Get rights and content

Abstract

We have devised a method of achieving the much-used macrocyclic polyether, 1,5-dinaphtho[38]crown-10, in three steps by a route that is more efficient and requires fewer purification procedures than those reported in the literature to date. The strategy can also be extended to the synthesis of asymmetric crown-10 ether derivatives with one 1,5-dinaphtho ring system.

Section snippets

Acknowledgment

This material is based upon work supported by the National Science Foundation under CHE-0924620.

References and notes (19)

  • C.J. Pedersen

    J. Am. Chem. Soc.

    (1967)
    C.J. Pedersen

    J. Am. Chem. Soc.

    (1967)
    C.J. Pedersen

    Aldrichim. Acta

    (1971)
    C.J. Pedersen

    Angew. Chem., Int. Ed. Engl.

    (1988)
  • D.J. Cram

    Angew. Chem., Int. Ed. Engl.

    (1988)
  • J.-M. Lehn

    Angew. Chem., Int. Ed. Engl.

    (1988)
  • M.C.T. Fyfe et al.

    Acc. Chem. Res.

    (1997)
    S.J. Cantrill et al.

    J. Chem. Soc., Dalton Trans.

    (2000)
    Q. Li et al.

    Science

    (2009)
  • D. Philp et al.

    Angew. Chem., Int. Ed. Engl.

    (1996)
    C.-P. Chak et al.

    ACS Nano

    (2009)
  • B.L. Allwood et al.

    J. Chem. Soc., Chem. Commun.

    (1987)
    B.L. Allwood et al.

    J. Chem. Soc., Chem. Commun.

    (1987)
    P.R. Ashton et al.

    J. Chem. Soc., Chem. Commun.

    (1987)
  • S. Anderson et al.

    Acc. Chem. Res.

    (1993)
    J.F. Stoddart et al.

    Proc. Natl. Acad. Sci. U.S.A.

    (2002)
    K.E. Griffiths et al.

    Pure Appl. Chem.

    (2008)
  • D.B. Amabilino et al.

    Chem. Rev.

    (1995)
    J.F. Stoddart et al.

    Tetrahedron

    (2008)
    J.F. Stoddart

    Chem. Soc. Rev.

    (2009)
  • P.R. Ashton et al.

    Tetrahedron Lett.

    (1987)
    D.G. Hamilton et al.

    Chem. Eur. J.

    (1998)
    D.B. Amabilino et al.

    J. Am. Chem. Soc.

    (1998)
There are more references available in the full text version of this article.

Cited by (0)

View full text