Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization

Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization

The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C−H functionalization of a pyridine moiety to...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 132; no. 17; pp. 5926 - 5927
Main Authors: Fischer, Daniel F, Sarpong, Richmond
Format: Journal Article
Language:English
Published: United States American Chemical Society 05-05-2010
Subjects:
Carbon - chemistry
Catalysis
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Hydrogen - chemistry
Iridium - chemistry
Lycopodium - metabolism
Pyridines - chemistry
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Summary:The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C−H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja101893b