4.8 Article

Synthesis of Fused Carbocycles via a Selective 6-Endo Dig Gold(I)-Catalyzed Carbocyclization

Journal

ORGANIC LETTERS
Volume 13, Issue 20, Pages 5580-5583

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol202314q

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Funding

  1. Natural Science and Engineering Research Council of Canada (NSERC) [CGS-D1]
  2. Merck Research Laboratories
  3. Merck-Frosst Canada
  4. Boehringer Ingelheim (Laval)
  5. PREA
  6. Canada Foundation for Innovation
  7. Ontario Innovation Trust
  8. University of Ottawa

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A gold-catalyzed synthesis of fused carbocycles via a regioselective 6-endo dig process is reported. The selectivity can be modulated by the steric and electronic properties of gold(I) complexes. The ligands can influence the pathway selectivity for the first bond formation rather than through a common intermediate generated after an Initial bond formation. This gold(I)-catalyzed transformation provides access to synthetically useful carbocyclic motifs that are found in numerous diterpenoid natural products.

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