Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds

RE Gawley, GA Smith

Index: Gawley, Robert E.; Smith, Gregory A. Arkivoc, 2011 , vol. 2011, # 5 p. 167 - 179

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Abstract

Abstract Asymmetric alkylation of enantiomeric tetrahydroisoquinolyl oxazolines was achieved with 96–97% diastereoselectivity. Removal of the oxazoline chiral auxiliary and further transformations provide a straightforward synthesis of the two synthetic intermediates that were previously synthesized by resolution, and which comprise a formal synthesis of berbamunine by Ullman coupling.