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Paper | Special issue | Vol 97, No. 1, 2018, pp.459-477
Published online, 16th March, 2018
DOI: 10.3987/COM-18-S(T)36
Oxidation of 1-Arylcyclohexa-2,5-dienes and Subsequent Double Michael Addition. A Rapid Access to the Büchi Ketone and the Pentacyclic Core of Aspidosperma Alkaloids

Dawood Hosni Ibrahim, Julie Dunet, Frédéric Robert, and Yannick Landais*

*Institute of Molecular Sciences, University of Bordeaux, 351 Cours de la Libération, F-33405 Talence Cedex, France

Abstract

The Pd-catalyzed oxidation of 1-arylcyclohexa-2,5-dienes, resulting from a Birch reductive alkylation, leads to the corresponding arylcyclohexadienones. A careful choice of the substituents on the starting biaryl affords arylcyclohexadieonones, which may then enter into a double Michael addition, opening an access to the tetracyclic core of terpene indole alkaloids of the aspidosperma family. This strategy was used to prepare the Büchi ketone, a key-intermediate in the synthesis of this class of alkaloids, in 6 synthetic operations and 17% overall yield from commercially available 2-aminobiphenyl.