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

A straightforward method for indenone synthesis was achieved by Pd/NBE‐catalyzed annulation between simple aryl iodides and unsaturated carboxylic acid anhydrides. This method enabled streamlined syntheses of pauciflorol F and acredinone A.

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.

from A via a.sfakia on Inoreader http://bit.ly/2LN5USC