4.7 Article

Synthesis of the Tetracyclic Core (ABCE Rings) of Daphenylline

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 18, Pages 8367-8373

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo301533f

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Funding

  1. NSFC [21125207, 21072086, 21102062]
  2. MOST [2010CB833200]
  3. Program 111

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A concise synthesis of the tetracyclic core (ABCE rings) of daphenylline has been accomplished involving a benzobicyclo[3.3.1] lactam as the key intermediate. This bridged bicyclic intermediate was efficiently constructed via a Bronsted acid promoted intramolecular Friedel-Crafts type Michael addition of a delta-benzyl alpha,beta-unsaturated delta-lactam.

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