Intramolecular Heck cyclization to the galanthamine-type alkaloids: Total synthesis of (±)-lycoramine
Journal
Tetrahedron
Journal Volume
60
Journal Issue
50
Pages
11655
Date Issued
2004-12-06
Author(s)
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. Graphical Abstract. © 2004 Elsevier Ltd. All rights reserved.
Subjects
Galanthamine | Heck reaction | Intramolecular cyclization | Lycoramine
Type
journal article