Total Synthesis of (−)-Galanthamine by Remote Asymmetric Induction

A pivotal intramolecular Michael addition to form a fused 5,7,5 ring system and the skeleton of (−)‐galanthamine (1) was completely controlled by a remote chiral imidazolidinone auxiliary derived from D‐phenylalanine (see scheme). This total synthesis of the allylic alcohol 1 avoids the correspondin...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2004-05, Vol.43 (20), p.2659-2661
Main Authors: Kodama, Sumiaki, Hamashima, Yoshio, Nishide, Kiyoharu, Node, Manabu
Format: Article
Language:English
Subjects:
alkaloids
asymmetric synthesis
Galantamine - chemical synthesis
Michael addition
Models, Chemical
Molecular Structure
natural products
Parasympathomimetics - chemical synthesis
Stereoisomerism
total synthesis
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Summary:A pivotal intramolecular Michael addition to form a fused 5,7,5 ring system and the skeleton of (−)‐galanthamine (1) was completely controlled by a remote chiral imidazolidinone auxiliary derived from D‐phenylalanine (see scheme). This total synthesis of the allylic alcohol 1 avoids the corresponding enone narwedine, a highly allergenic intermediate in previous syntheses of 1.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353636