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  • Title: Diastereoselective construction of quaternary carbons directed via macrocyclic ring conformation: formal synthesis of (-)-mesembrine.
    Author: Arns S, Lebrun ME, Grisé CM, Denissova I, Barriault L.
    Journal: J Org Chem; 2007 Nov 23; 72(24):9314-22. PubMed ID: 17958376.
    Abstract:
    In this article, we report a highly diastereoselective new method for the generation of quaternary carbon centers through an anionic oxy-Cope/alkylation sequence where the diastereoselectivity is induced by the conformation of a macrocyclic tetrasubstituted enolate. The use of our methodology culminated in the formal total synthesis of (-)-mesembrine (34) in 11 steps from known starting materials.
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