Elsevier

Tetrahedron

Volume 52, Issue 21, 20 May 1996, Pages 7391-7420
Tetrahedron

Development of modified Pauson-Khand reactions with ethylene and utilisation in the total synthesis of (+)-taylorione

This paper is dedicated to the memory of our dear friend and colleague Gavin S. Forsyth (24.1.70-19.12.93).
https://doi.org/10.1016/0040-4020(96)00259-1Get rights and content

Abstract

Two complementary Pauson-Khand annulation protocols for use with the gaseous alkene, ethylene, are described. These N-oxide promoted reactions (10 examples) are shown to proceed under both mild autoclave conditions or, more conveniently, at atmospheric pressure. The developed methodology has been utilised as the key transformation in the total synthesis of the sesquiterpene (+)-taylorione which has been realised in a good overall yield from readily available (+)-2-carene.

The development of mild Pauson-Khand techniques for use with ethylene are described; the total synthesis of (+)-taylorione 1 is achieved in high yield by use of the novel protocols in the key transformation.

  1. Download : Download full-size image

References (58)

  • N.E. SchoreN.E. Schore

    Organic Reactions

    (1991)
    P.L. Pauson et al.

    Ann. N. Y. Acad. Sci.

    (1977)
    P.L. Pauson

    Tetrahedron

    (1985)
  • A. Matsuo et al.

    J. Chem. Soc., Perkin Trans. 1

    (1979)
  • A. Speicher et al.

    Synthesis

    (1995)
  • C. Johnstone et al.

    J. Chem. Soc., Chem. Commun.

    (1995)
  • A.R. Gordon et al.

    Synlett

    (1995)
  • W. Cocker et al.

    J. Chem. Soc., Perkin Trans. 1

    (1975)
  • L.I. Zakharkin et al.

    J. Gen. Chem. USSR

    (1964)
  • D.C. Billington et al.

    J. Chem. Res.

    (1988)
    D.C. Billington et al.

    J. Chem. Res.

    (1988)
  • V.A. Maksakov et al.

    J. Organomet. Chem.

    (1995)
  • W.J. Kerr et al.

    Synlett

    (1995)
  • A.M. Hay et al.

    Organometallics

    (1995)
  • C.R. Johnson et al.

    J. Org. Chem.

    (1987)
    D.J. Peterson

    J. Org. Chem.

    (1968)
    T. Imamoto et al.

    J. Org. Chem.

    (1984)
  • G.A. Olah et al.

    J. Org. Chem.

    (1983)
  • S.H. Wu et al.

    Synth. Commun.

    (1994)
  • G. Balme et al.

    J. Org. Chem.

    (1983)
  • B.H. Lipshutz et al.

    Synth. Commun.

    (1982)
  • T. Nishiguchi et al.

    J. Chem. Soc., Chem. Commun.

    (1995)
  • D.H.R. Barton et al.

    J. Chem. Soc., Chem. Commun.

    (1971)
  • A. Oku et al.

    Chem. Lett.

    (1993)
  • K. Tanemura et al.

    J. Chem. Soc., Chem. Commun.

    (1992)
  • S.V. Ley et al.

    Synthesis

    (1994)
  • T. Cohen et al.

    J. Org. Chem.

    (1985)
  • V. Bernardes et al.

    J. Org. Chem.

    (1995)
    A.L. Veretenov et al.

    Tetrahedron Lett.

    (1995)
    T.F. Jamison et al.

    J. Am. Chem. Soc.

    (1994)
    N. Naz et al.

    Tetrahedron Lett.

    (1994)
    J. Marco-Contelles

    Tetrahedron Lett.

    (1994)
    M.E. Krafft et al.

    Tetrahedron Lett.

    (1994)
    D.L.J. Clive et al.

    J. Org. Chem.

    (1994)
    N. Jeong et al.

    Tetrahedron Lett.

    (1993)
    S. Yoo et al.

    Tetrahedron Lett.

    (1993)
    A. van der Waals et al.

    J. Chem. Soc., Chem. Commun.

    (1992)
    S. Takano et al.

    J. Chem. Soc., Chem. Commun.

    (1992)
    E.G. Rowley et al.

    J. Org. Chem.

    (1992)
    A.S. Gybin et al.

    J. Am. Chem. Soc.

    (1992)
    M.E. Krafft et al.

    Tetrahedron Lett.

    (1992)
    S. Takano et al.

    Chem. Lett.

    (1992)
    A.L. Veretenov et al.

    Tetrahedron Lett.

    (1991)
    W.A. Smit et al.

    Tetrahedron Lett.

    (1991)
    E.G. Rowley et al.

    J. Organomet. Chem.

    (1991)
    M. Thommen et al.

    Chimia

    (1991)
    J. Castro et al.

    J. Am. Chem. Soc.

    (1990)
    A. de Meijere et al.

    Synlett

    (1990)
    W.G. Dauben et al.

    Tetrahedron Lett.

    (1990)
    M.E. Price et al.

    J. Org. Chem.

    (1989)
    P. Magnus et al.

    J. Org. Chem.

    (1989)
    M.E. Price et al.

    Tetrahedron Lett.

    (1989)
    N.E. Schore et al.

    J. Am. Chem. Soc.

    (1988)
    J. Mulzer et al.

    Justus Liebigs Ann. Chem.

    (1988)
    C. Almansa et al.

    Tetrahedron

    (1988)
    C. Almansa et al.

    Synth. Commun.

    (1988)
    P. Magnus et al.

    J. Am. Chem. Soc.

    (1987)
    V. Sampath et al.

    J. Org. Chem.

    (1987)
    P. Magnus et al.

    J. Org. Chem.

    (1987)
    N.E. Schore et al.

    J. Org. Chem.

    (1987)
    D.C. Billington et al.

    J. Organomet. Chem.

    (1987)
    D.H. Hua et al.

    Tetrahedron Lett.

    (1987)
    D.H. Hua

    J. Am. Chem. Soc.

    (1986)
    E. Carceller et al.

    Tetrahedron

    (1986)
    B.E. La Belle et al.

    J. Org. Chem.

    (1985)
    A.-M. Montãna et al.

    Tetrahedron

    (1985)
    P. Magnus et al.

    Tetrahedron

    (1985)
    E. Carceller et al.

    Tetrahedron Lett.

    (1985)
    S. Kenaniyan et al.

    Angew. Chem., Int. Ed. Engl.

    (1985)
    M.J. Knudsen et al.

    J. Org. Chem.

    (1984)
    L. Daalman et al.

    J. Chem.Res.

    (1984)
    L. Daalman et al.

    J. Chem. Res.

    (1984)
    C. Exon et al.

    J. Am. Chem. Soc.

    (1983)
    D.C. Billington

    Tetrahedron Lett.

    (1983)
    H.J. Jaffer et al.

    J. Chem. Res.

    (1983)
    H.J. Jaffer et al.

    J. Chem. Res.

    (1983)
    D.C. Billington et al.

    Organometallics

    (1982)
    R.F. Newton et al.

    J. Chem. Res.

    (1980)
    R.F. Newton et al.

    J. Chem. Res.

    (1980)
  • A. Matsuo et al.

    Tetrahedron Lett.

    (1974)
  • M. Nakayama et al.

    Chem. Lett.

    (1979)
  • D.C. Billington et al.

    J. Organomet. Chem.

    (1988)
  • G.B. Hammond et al.

    J. Org. Chem.

    (1990)
  • H.C. Brown et al.

    J. Org. Chem.

    (1987)
  • Cited by (0)

    1

    Participating in the ECTS-Pilot Scheme of the EC Erasmus Programme. Resident University: Utrecht University, Department of Metal-Mediated Synthesis, Debye Institute, Padualaan 8,3584 CH Utrecht, The Netherlands.

    2

    Present address: Zeneca Pharmaceuticals, Alderly Park, Mereside, Cheshire, SK10 4TG, U.K.

    3

    Participating in the ECTS-Pilot Scheme of the EC Erasmus Programme. Resident University: Institut für Organische Chemie der Technischen Universität Berlin, Strasse des 17. Juni 135, 10623 Berlin, Germany.

    View full text