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Paper | Regular issue | Vol 32, No. 6, 1991, pp.1143-1151
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5710
A Highly Stereoselective Synthesis of (±)-Normalindine

Allan W. Rey, Walter A. Szarek,* and David B. MacLean*

*Department of Chemistry, Queen‘s University, Kingston, Ontario K6L 3N6, Canada

Abstract

Methyllithium reacted with (±)-dihydronaucléfine (5) to form, upon alkaline processing, a mixture of compounds, one having an exocyclic methylene group at C-5 (9) and the other, a C-5 — N iminiun compound having a methyl group at C-5 (10). Treatment of this mixture with either hydrogen over palladium catalyst or cyanoborohydride provided (±)-normalindine [(±)-1] in a highly stereoselective and efficient manner.