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

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

Research output: Contribution to journalArticle

22 Citations (Scopus)

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

Cite this

Intramolecular Heck cyclization to the galanthamine-type alkaloids: total synthesis of (±)-lycoramine. / Liang, Pi-Hui; Liu, Jing-Ping; Hsin, Ling-Wei; Cheng, Chen-Yu.

In: Tetrahedron, Vol. 60, No. 50, 06.12.2004, p. 11655-11660.

Research output: Contribution to journalArticle

Liang, Pi-Hui ; Liu, Jing-Ping ; Hsin, Ling-Wei ; Cheng, Chen-Yu. / Intramolecular Heck cyclization to the galanthamine-type alkaloids: total synthesis of (±)-lycoramine. In: Tetrahedron. 2004 ; Vol. 60, No. 50. pp. 11655-11660.
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