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Radical Reactions for Use in Organic Synthesis

  • Jeff Dener
  • David J. Hart
  • Horng-Chih Huang
  • Frank Seely
  • Shung Wu
Conference paper

Abstract

The notion that intramolecular free radical carbon-carbon bond-forming reactions might be of use in the synthesis of natural products of modest complexity was introduced by the Julia group in the 1960’s.1 The 1980’s have born witness to a rebirth of this idea and free radical cyclizations are now being used regularly in synthesis design.2,3 Our research in this area has focused on the development α-acylamino radical cyclizations for use in alkaloid synthesis4 and β-acyloxy radical cyclizations for use in terpenoid synthesis.5 The first portion of this lecture will describe the development of such reactions for use in total or partial syntheses of heliotridine (1→2), gelsemine (3→4) and pleurotin (5→6).2 In each case, the radical cyclization accomplishes a carbon-carbon bond construction that would be problematic using classical polar bond-forming reactions.

Keywords

Free Radical Organic Synthesis Radical Cyclization Chain Mechanism Free Radical Process 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Julia M (1964) Rec Chem Prog 25:1Google Scholar
  2. 2.
    Giese B (1986) Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, New YorkGoogle Scholar
  3. 3.
    Ramaiah M (1987) Tetrahedron 43:3541CrossRefGoogle Scholar
  4. 4.
    Hart DJ, Tsai Y-M (1982) J Am Chem Soc 104:1430CrossRefGoogle Scholar
  5. 5.
    Chuang C-P, Hart DJ (1983) J Org Chem 48:1782CrossRefGoogle Scholar
  6. 6.
    Hart DJ, Huang H-C (1988) J Am Chem Soc 110:1634CrossRefGoogle Scholar
  7. 7.
    Hart DJ, Seely FL (1988) J Am Chem Soc 110:1631CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1988

Authors and Affiliations

  • Jeff Dener
    • 1
  • David J. Hart
    • 1
  • Horng-Chih Huang
    • 1
  • Frank Seely
    • 1
  • Shung Wu
    • 1
  1. 1.Department of ChemistryThe Ohio State UniversityColumbusUSA

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