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  • Title: Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide.
    Author: Adlington RM, Baldwin JE, Mayweg AV, Pritchard GJ.
    Journal: Org Lett; 2002 Aug 22; 4(17):3009-11. PubMed ID: 12182611.
    Abstract:
    [reaction: see text] A study toward a possible biomimetic hetero Diels-Alder reaction is reported between humulene and a novel tropolone ortho-quinone methide. A suitable tropolone ortho-quinone methide precursor has been prepared from 3-methyl-2-furoate. Heating the ortho-quinone methide precursor gave a tropolone ortho-quinone methide, which in the presence of humulene underwent a hetero Diels-Alder reaction to give a deoxy analogue of epolone B.
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