4.7 Article

De novo synthesis of (+)-isofregenedol

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 18, Pages 7436-7439

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo801365z

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Funding

  1. University of Ottawa
  2. NSERC
  3. Merck Frosst Canada
  4. Merck and Co.
  5. Boehringer Ingelheim
  6. PREA
  7. Le Fonds Quebecois de la Recherche sur la Nature et les Technologies (FQRNT)

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An efficient enantioselective synthesis of (+)-isofregenedol was achieved in 13 steps from commercially available cyclohexene oxide without the use of protecting groups. The tetrahydronaphthalenic core of isofregenedol was obtained via a gold(I)-catalyzed benzannulation recently developed in our laboratory.

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