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

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

Feipeng Liu  1   2 , Zhe Dong  1 , Jianchun Wang  1 , Guangbin Dong  1
Affiliations

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

Feipeng Liu et al. Angew Chem Int Ed Engl. .

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.

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Figures

Scheme 1.
Scheme 1.
Indenone/indanone containing natural products and indenone synthesis
Scheme 2.
Scheme 2.
Further reaction exploration
Scheme 3.
Scheme 3.
Mechanistic exploration
Scheme 4.
Scheme 4.
Formal synthesis of pauciflorol F.
Scheme 5.
Scheme 5.
Retrosynthetic analysis of acredinone A.
Scheme 6.
Scheme 6.
Total synthesis of acredinone A.
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