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

Pi-Hui Liang, Jing-Ping Liu, Ling-Wei Hsin, Chen-Yu Cheng

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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.
Original languageTraditional Chinese
Pages (from-to)11655-11660
Number of pages6
JournalTetrahedron
Volume60
Issue number50
DOIs
Publication statusPublished - Dec 6 2004
Externally publishedYes

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