Palladium-catalyzed synthesis of 2-alkenyl-3-arylindoles via a dual α-arylation strategy: formal synthesis of the antilipemic drug fluvastatin?

Organic & Biomolecular Chemistry Pub Date: 2015-09-18 DOI: 10.1039/C5OB01632K

Abstract

A new approach has been developed for the synthesis of substituted 2-alkenyl-3-arylindoles. The strategy comprises palladium-catalyzed dual α-arylation of TES-enol ethers of enones as the key step. This methodology results in products with very good yields and the regioselectivity is exclusive. We have also successfully used this dual α-arylation methodology in the formal synthesis of the cholesterol-lowering drug fluvastatin.

Graphical abstract: Palladium-catalyzed synthesis of 2-alkenyl-3-arylindoles via a dual α-arylation strategy: formal synthesis of the antilipemic drug fluvastatin
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