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Synlett 1997; 1997(1): 75-78
DOI: 10.1055/s-1997-693
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The Synthesis of Functionalized Pyrrolo-[2,1-c][1,4]-Benzodiazepines

Ian A. O'Neil1 , Clare L. Murray1 , Rachel C. Hunter1 , S. Barret Kalindjian2 , Terry C. Jenkins3
  • 1Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, P.O.Box 147, Liverpool L69 3BX, U.K.
  • 2James Black Foundation, 68, Half Moon Lane, Dulwich, London SE 24 9JE, U.K.
  • 3CRC Biomolecular Structure Unit, Institute of Cancer Research, Sutton, Surrey SM2 5NG, U.K.
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Publication Date:
22 March 2004 (online)

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Two concise and high yielding routes to the antitumour antibiotic pyrrolo-[2,1-c][1,4]-benzodiazepine ring system are described. Thus, condensation of prolinol with 2-azidobenzoylchloride gives the tertiary amide (3). Oxidation to the aldehyde (4) followed by generation of the phosphoroimine by Staudinger reaction results in ring closure via an aza-Wittig reaction to yield the desired ring system. Alternatively, coupling of prolinol with the appropriate isatoic anhydride yields the corresponding amino alcohol. Oxidation with Dess-Martin periodinane yields the PBDs in moderate to good yield.

pyrrolo-[2,1-c][1,4]-benzodiazepine - Dess-Martin periodinane - palladium coupling - DNA binding

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