Intramolecular Heck cyclization to the galanthamine-type alkaloids: total synthesis of (±)-lycoramine

Furan Michael reaction Heck Reaction Intramolecular reaction Annulation
DOI: 10.1016/j.tet.2004.09.044 Publication Date: 2004-10-05T15:09:06Z
ABSTRACT
Abstract A novel approach towards the construction of the galanthamine skeleton was demonstrated by the total synthesis of (±)-lycoramine. The key steps include a Pd-catalyzed intramolecular cyclization to form the seven-membered azepane ring and a spontaneous intramolecular Michael addition to afford the five-membered furan ring. This synthetic route has also been demonstrated to be useful for the preparation of novel derivatives with simplified galanthamine skeletons.
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