Asymmetric Total Synthesis of (−)-Leuconoxine via Chiral Phosphoric Acid Catalyzed Desymmetrization of a Prochiral Diester

The asymmetric total synthesis of (−)-leuconoxine has been achieved. The desymmetrization of a prochiral diester using a chiral phosphoric acid catalyst produced a highly enantioenriched lactam with excellent yield. The ring construction featuring an intramolecular N-acyliminium cyclization and the...

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Bibliographic Details
Published in:Organic letters 2015-01, Vol.17 (1), p.154-157
Main Authors: Higuchi, Kazuhiro, Suzuki, Shin, Ueda, Reeko, Oshima, Norifumi, Kobayashi, Emiko, Tayu, Masanori, Kawasaki, Tomomi
Format: Article
Language:English
Subjects:
Apocynaceae - chemistry
Catalysis
Cyclization
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Molecular Structure
Phosphoric Acids - chemistry
Pyrrolidinones - chemical synthesis
Pyrrolidinones - chemistry
Stereoisomerism
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Summary:The asymmetric total synthesis of (−)-leuconoxine has been achieved. The desymmetrization of a prochiral diester using a chiral phosphoric acid catalyst produced a highly enantioenriched lactam with excellent yield. The ring construction featuring an intramolecular N-acyliminium cyclization and the one-step pyrrolidone formation using Bestmann’s ylide was successfully accomplished.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5033865