Total Synthesis of (S)-(+)-Imperanene. Effective Use of Regio- and Enantioselective Intramolecular Carbon−Hydrogen Insertion Reactions Catalyzed by Chiral Dirhodium(II) Carboxamidates

The total synthesis of (S)-(+)-imperanene, a natural product found in Chinese medicine, has been completed in 12 steps from a commercially available cinnamic acid. The key step is highly enantioselective carbon−hydrogen insertion from a diazoacetate using a chiral dirhodium(II) carboxamidate catalys...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-05, Vol.67 (9), p.2954-2959
Main Authors: Doyle, Michael P, Hu, Wenhao, Valenzuela, Marcela V
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Chemistry
Cinnamates - chemistry
Exact sciences and technology
Magnetic Resonance Spectroscopy
Medicine, Chinese Traditional
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Organometallic Compounds - chemistry
Phenols - chemical synthesis
Phenols - chemistry
Plants, Medicinal - chemistry
Preparations and properties
Rhodium - chemistry
Stereoisomerism
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Summary:The total synthesis of (S)-(+)-imperanene, a natural product found in Chinese medicine, has been completed in 12 steps from a commercially available cinnamic acid. The key step is highly enantioselective carbon−hydrogen insertion from a diazoacetate using a chiral dirhodium(II) carboxamidate catalyst. An elimination process essential to the construction has been optimized to avoid intramolecular Friedel−Crafts alkylation.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo016220s