4.8 Article

Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral lodane

Journal

ORGANIC LETTERS
Volume 18, Issue 5, Pages 1120-1123

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00224

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Funding

  1. Agence Nationale de la Recherche [ANR-10-BLAN-0721]
  2. Ministere de la Recherche
  3. CNRS
  4. Conseil Regional d'Aquitaine
  5. Agence Nationale de la Recherche (ANR) [ANR-10-BLAN-0721] Funding Source: Agence Nationale de la Recherche (ANR)

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The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphenol using a novel C-2-symmetrical chiral Salen-type bis(lambda(5)-iodane).

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