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Synlett 1995; 1995(SI): 547-548
DOI: 10.1055/s-1995-5266
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Synthetic Studies on Pancratistatin. Construction of the Phenanthridone Ring System via a Hydrogen Bond Controlled Enamide Photocyclization

James H. Rigby* , Vinay Gupta
  • *Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA
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Publication Date:
31 December 2000 (online)

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Synthesis of the phenanthridone core of the antineoplastic alkaloid pancratistatin is reported. The key step is a regiocontrolled aryl enamide photocyclization that produces the trans-BC ring fusion characteristic of the natural product.

pancratistatin - phenanthridone - enamide - photocyclization - hydrogen-bonding