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Premium Total Synthesis of (−)‐Galanthamine by Remote Asymmetric Induction
Kodama Sumiaki,
Hamashima Yoshio,
Nishide Kiyoharu,
Node Manabu
Publication year2004
Publication title
angewandte chemie international edition
Resource typeJournals
PublisherWILEY‐VCH Verlag
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 .
Subject(s)allylic rearrangement , catalysis , chemistry , computer science , enone , intramolecular force , mathematical analysis , mathematics , organic chemistry , ring (chemistry) , scheme (mathematics) , stereochemistry , total synthesis
SCImago Journal Rank5.831

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