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  • Title: The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence.
    Author: Malachowski WP, Paul T, Phounsavath S.
    Journal: J Org Chem; 2007 Aug 31; 72(18):6792-6. PubMed ID: 17676911.
    Abstract:
    The first enantioselective synthesis of (-)-lycoramine has been achieved in 14 steps and 5% overall yield from the biaryl derivative 1. The synthesis applies the previously developed Birch-Cope sequence to create the key arylic quaternary stereocenter of (-)-lycoramine with excellent enantioselective control. The product of the Birch-Cope sequence, a versatile 4,4-disubstituted-2-carboxamide-2-cyclohexen-1-one, was elaborated through an intramolecular conjugate addition of a phenol to create the dihydrofuran ring. Chemoselective elaboration of the allyl group into an amide followed by a modified Pictet-Spengler reaction generated the azepine ring.
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