4.8 Article

Gold-Catalyzed Photoredox C(sp2) Cyclization: Formal Synthesis of (±)-Triptolide

Journal

ORGANIC LETTERS
Volume 18, Issue 11, Pages 2592-2595

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00968

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Funding

  1. Natural Sciences and Engineering Research Council (NSERC)
  2. Vision postdoctoral scholarships

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Photoexcitation of ditheric gold Complex showed the activation of a C(sp(2)) -Br bond to generate a vinyl radical in a mild photoredbx catalysis process. Use of [Au-2(dppm)2] Cl-2 with 365 nm LEDs in a photoredox catalysis process to produce polycyclic scaffolds using vinyl radicals is reported. This method achieved the synthesis of a small library of butenolide polycyclic compounds and naphthol polycyclic compounds. The efficacy of this photoredox process was further demonstrated by accomplishing the concise formal synthesis of (+/-)-triptolide.

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