Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A

Angew Chem Int Ed Engl. 2019 Feb 11;58(7):2144-2148. doi: 10.1002/anie.201813699. Epub 2019 Jan 16.

Abstract

To show the synthetic utility of palladium/norbornene (Pd/NBE) cooperative catalysis, here we report concise syntheses of indenone-based natural products, pauciflorol F and acredinone A, which are enabled by direct annulation between aryl iodides and unsaturated carboxylic acid anhydrides. Compared to the previous indenone-preparation approaches, this method allows simple aryl iodides to be used as substrates with complete control of the regioselectivity. The total synthesis of acredinone A features two different Pd/NBE-catalyzed ortho acylation reactions for constructing penta-substituted arene cores, including the development of a new ortho acylation/ipso borylation.

Keywords: acredinone A; indenone; norbornene; palladium; pauciflorol F.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzophenones / chemical synthesis*
  • Benzophenones / chemistry
  • Catalysis
  • Hydrocarbons, Iodinated / chemistry*
  • Indenes / chemical synthesis*
  • Indenes / chemistry
  • Molecular Structure
  • Norbornanes / chemistry*
  • Palladium / chemistry*
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry

Substances

  • Benzophenones
  • Hydrocarbons, Iodinated
  • Indenes
  • Norbornanes
  • Stilbenes
  • acredinone A
  • pauciflorol F
  • Palladium