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

Kodama Sumiaki | Zendy; Hamashima Yoshio | Zendy; Nishide Kiyoharu | Zendy; Node Manabu | Zendy

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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 .

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