Photochemical and Thermal Bergman Cyclization of a Pyrimidine Enediynol and Enediynone

Nakyen Choy,† Beatriz Blanco,† Jenghai Wen,‡ Awtar Krishan,‡ and K. C. Russell*†
Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33124, and Department Of Radiation Oncology (R-71), University of Miami, P.O. Box 016960, Miami, Florida 33101
Org. Lett., 2000, 2 (24), pp 3761–3764
DOI: 10.1021/ol006061j
Publication Date (Web): November 5, 2000
Copyright © 2000 American Chemical Society
†

 Department of Chemistry.

,
‡

 Department of Radiation Oncology.

,
*

 Phone (305)284-6856. Fax (305)284-1880.

, krussell@umiami.ir.miami.edu

Abstract

Abstract Image

Novel 10-membered pyrimidine enediynes (3 and 4) were synthesized in seven and eight steps, respectively. These compounds were compared for their abilities to undergo Bergman cyclization both thermally and photochemically. Alcohol 3 readily cyclized both thermally and photochemically in iPrOH, while ketone 4 only showed efficient thermal cyclization. Both compounds were also shown to cleave dsDNA under the appropriate conditions.

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History

  • Published In Issue November 30, 2000
  • Received May 15, 2000
    Revised October 20, 2000

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