Palladium-Catalyzed Intramolecular Oxidative Heck Cyclization and Its Application toward a Synthesis of (±)-β-Cuparenone Derivatives Supported by Computational Studies

Abstract

A novel and efficient intramolecular oxidative cyclization of substituted homoallylic alcohols to form cyclic keto compounds under palladium-catalyzed conditions is described. The reaction has practical applications in the synthesis of sesquiterpenes. The mechanism of cyclization, the key step in the tandem reaction­, was analyzed by using density functional theory calculations.

Key words

palladium - Heck reaction - cyclizations - terpenoids - ketones­ - alkenes - catalysis - oxidations - computational studies

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