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Synthesis 1994; 1994(7): 703-708
DOI: 10.1055/s-1994-25553
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Cycloaddition of Cross-Conjugated Trienes to Halogenated Quinones

Michel Couturier* , Paul Brassard
  • *Départment de chimie, Université Laval, Québec G1K 7P4, Canada
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Publication Date:
17 September 2002 (online)

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The chemoselectivity of [4 + 2] cycloadditions involving electronrich cross-conjugated trienes and halogenated quinones has been examined. The approach provides improved preparations of 6-acetyl-2,3,7-trihydroxyjuglone, solorinic and norsolorinic acids, and averythrin. It also confirms the structure proposed for haematommone and 3,8-dihydroxy-4-methoxy-2-methoxycarbonyl-1-methyl-anthraquinone but invalidates that of sopheranin.