Portal de Periódicos da CAPES

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

2004; Wiley; Volume: 43; Issue: 20 Linguagem: Inglês

10.1002/anie.200353636

1521-3773

Sumiaki Kodama, Yoshio Hamashima, Kiyoharu Nishide, Manabu Node,

Alkaloids: synthesis and pharmacology

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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53636_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.