The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence.

William P Malachowski, Tapas Paul, Sophia Phounsavath

Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, USA. wmalacho@brynmawr.edu

The Journal of organic chemistry 2007 Aug 31

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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.

Citation

William P Malachowski, Tapas Paul, Sophia Phounsavath. The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence. The Journal of organic chemistry. 2007 Aug 31;72(18):6792-6