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Synlett 1991; 1991(8): 586-588
DOI: 10.1055/s-1991-20807
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An Organometallic Approach for the Synthesis of Lycorine: Substituent Tolerance in the Arylation Step

G. Richard Stephenson* , Ian M. Palotai, William J. Ross, David E. Tupper
  • *School of Chemical Sciences, University of East Anglia, Norwich, NR4 7TJ, England
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Publication Date:
07 March 2002 (online)

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The coupling of diarylzinc and cuprate reagents with tricarbonyl (2-methoxycyclohexadienylium)iron hexafluorophosphate has been examined in studies which indicate that the efficiency of the coupling step is crucially dependant on the substitution pattern on the aromatic ring. The coupling reaction has been used for the construction of an important chiral centre in model studies for an organometallic route to lycorine. When the aromatic ring bears both methylenedioxy and CH2OCH2CH=CH2 groups, either organozinc or cuprate methods could be used, but when the CH2N(CH2CH=CH2)2 analogue was used, only the cuprate reagent afforded the coupling product in a satisfactory yield.

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