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Synlett 2001; 2001(3): 0436-0438
DOI: 10.1055/s-2001-11408
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The Diels-Alder Reactions of Quinone Imine Ketals: A Synthesis of The Ergot Skeleton

Scott C. Banfield* , Michael A. Kerr
  • *Department of Chemistry, University of Western Ontario, London, Ontario N6A 5B7, CA; Phone + 1(5 19)6 61-21 11 ext 8 63 54; E-mail: makerr@julian.uwo.ca
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Publikationsdatum:
31. Dezember 2001 (online)

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The high pressure (13 kbar) Diels-Alder reaction of N-benzoyl-p-benzoquinone-mono-imine dimethyl ketal with an appropriate diene yields, after treatment with anhydrous acid, a dihydronaphthanilide. Conversion to the tricyclic skeleton of the ergot alkaloids is effected via a series of simple transformations.

Diels-Alder reactions - quinones - alkaloids - cycloadditions