Intramolecular nickel catalyzed cycloadditions of bis-dienes: 3 approaches to the taxane skeleton☆

https://doi.org/10.1016/S0040-4039(00)96085-4Get rights and content

Abstract

The successful application of the nickel catalyzed, intramolecular [4+4] cycloaddition of bis-dienes to the preparation of both the AB and BC ring systems of the taxane diterpenes is described. This cycloaddition methodology provides the basis for a general and efficient route to angularly alkyl-substituted bicyclo[6.4.0]dodecanes and to bicyclo[5.3.1]undecanes.

The nickel catalyzed cycloaddition of bis-dienes is demonstrated to provide angularly alkyl-substituted bicyclo[6.4.0]dodecane and to bicyclo[5.3.1]undecanes. Models of both the AB and BC ring systems of the taxane diterpenes are described.

  1. Download : Download full-size image

References (9)

  • S.N. Balasubrahmanyam et al.

    J. Chem. Soc. (B)

    (1970)
  • R.W. Miller

    J. Nat Prod.

    (1980)
    M.C. Wani et al.

    J. Am. Chem. Soc.

    (1971)
    N.F. Magri et al.

    J. Org. Chem.

    (1986)
    D.G.I. Kingston et al.

    J. Nat. Prod.

    (1982)
    J. Parness et al.

    Biochem. Biophy. Res. Comm.

    (1982)
    P.B. Schiff et al.

    Nature

    (1979)
  • aStudies bearing on the syntheses of the taxanes have been reported from the laboratories of: Berkowitz, W.F.;...J.D. Winkler et al.

    J. Am. Chem. Soc.

    (1986)
    A.S. Kende et al.

    J. Am. Chem. Soc.

    (1986)
    C.S. Swindell et al.

    J. Org. Chem.

    (1986)
  • E. Negishi et al.

    J. Am. Chem. Soc.

    (1985)
    C.L. Rand et al.

    J. Org. Chem.

    (1981)
    E. Negishi et al.

    J. Am. Chem. Soc.

    (1978)
There are more references available in the full text version of this article.

Cited by (0)

☆

For previous work in this series, see: a) Wender, P.A.; and Ihle, N.C., J. Am. Chem. Soc. 1986, 108, 4678; b) Wender, P.A.; and Ihle, N.C., Tetrahedron Lett,, submitted for publication.

View full text
Copyright © 1987 Published by Elsevier Ltd.