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Total Synthesis of (−)‐Galanthamine by Remote Asymmetric Induction
Author(s) -
Kodama Sumiaki,
Hamashima Yoshio,
Nishide Kiyoharu,
Node Manabu
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200353636
Subject(s) - intramolecular force , scheme (mathematics) , ring (chemistry) , stereochemistry , computer science , total synthesis , allylic rearrangement , enone , chemistry , mathematics , organic chemistry , catalysis , mathematical analysis
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 .