Tetrahedron

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

PH Liang, JP Liu, LW Hsin, CY Cheng

Index: Liang, Pi-Hui; Liu, Jing-Ping; Hsin, Ling-Wei; Cheng, Chen-Yu Tetrahedron, 2004 , vol. 60, # 50 p. 11655 - 11660

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Citation Number: 17

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 ...

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