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Synlett 2001; 2001(6): 0765-0768
DOI: 10.1055/s-2001-14592
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Synthesis of Heteroarenes via Radical Cyclisation onto Nitriles

W. Russell Bowman* , Colin F. Bridge, Martin O. Cloonan, David C. Leach
  • *Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK; Fax + 44-1509 223 925; E-mail: w.r.bowman@lboro.ac.uk
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Publication Date:
31 December 2001 (online)

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A new protocol for the synthesis of tetracyclic nitrogen heteroarenes using cascade radical cyclisation has been developed. The key steps involve 5-exo vinyl radical cyclisation onto nitriles to yield intermediate iminyl radicals which cyclise onto an arene rings. Rings A-D of the anticancer alkaloids camptothecin, mappicine and nothapodytines A and B have been synthesised using this protocol.

radical cyclisation - nitriles - tandem reactions - vinyl radicals - camptothecin