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Baldwin, J.E. et al.

Baldwin, Mayweg, Neumann, Pritchard,

Studies toward the biomimetic synthesis of tropolone natural products via a hetero Diels-Alder reaction.

Analogues of the tropolone natural products pycnidione and epolone B were synthesized via a hetero Diels-Alder reaction of benzotropolone 10 with humulene. The quinone methide benzotropolone 13 was generated in situ by thermalisation of benzotropolone 10. Benzotropolone 10 was derived from phthalic acid via carbonyl ylide 8a followed by an intramolecular 1,3-dipolar cycloaddition and subsequent acid-catalyzed ring opening.[1]

References

Studies toward the biomimetic synthesis of tropolone natural products via a hetero Diels-Alder reaction. Baldwin, J.E., Mayweg, A.V., Neumann, K., Pritchard, G.J. Org. Lett. (1999) [Pubmed]

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