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The Pd-catalyzed Alder-ene reactions of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes as a new route to C3a-arylhexahydroindoles: towards the total synthesis of tazettine

Lehmann, Anna; Willis, Anthony; Banwell, Martin


A series of N-protected and propargylated 1-amino-2-aryl-2-cyclohexenes (4) has been prepared. Several of these have been shown to undergo an intramolecular Alder-ene reaction in the presence of palladium acetate and the ligand BBEDA to afford C3a-arylhexahydroindoles of the general form 1. Certain of these products may serve as precursors to the alkaloid tazettine (2).

CollectionsANU Research Publications
Date published: 2010
Type: Journal article
Source: Australian Journal of Chemistry
DOI: 10.1071/CH10359


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