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Synlett 1992; 1992(6): 507-509
DOI: 10.1055/s-1992-21396
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Hippeastrine Synthesis: Functionalised Metallated Arenes in an Organoiron Route to a Tricyclic Model

Stephen T. Astley* , G. Richard Stephenson
  • *School of Chemical Sciences, University of East Anglia, Norwich NR4 7TJ, England
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Publication Date:
08 March 2002 (online)

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Diarylcuprate reagents containing a functional group adjacent to the site of metallation have been employed as nucleophiles in reactions with cationic cyclohexadienyliron π-complexes. When a carboxylate group is situated ortho to the metallated position, the resulting dianionic species reacted exclusively in a C-C bond forming process. Lactone formation, using the carboxylate group as the second nucleophile, has been examined to demonstrate the role of the metal complexes as an organometallic dication equivalent in an organoiron entry to the antifeedant alkaloid hippeastrine.

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