Synthesis of Tetrahydropyrroloiminoquinone Alkaloids Based on Electrochemically Generated Hypervalent Iodine Oxidative Cyclization

An approach to the synthesis of the tetrahydropyrroloiminoquinone alkaloids has been developed and applied to the preparation of N-1-β-d-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization of aryl-methoxyamides by hypervalent iodine to construct the quinoline fra...

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Bibliographic Details
Published in:Organic letters 2010-02, Vol.12 (3), p.436-439
Main Authors: Inoue, Keisuke, Ishikawa, Yuichi, Nishiyama, Shigeru
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkaloids - pharmacology
Animals
Catalysis
Drug Resistance, Neoplasm - drug effects
Drug Screening Assays, Antitumor
Female
Humans
Iodobenzenes - chemistry
KB Cells
Marine Biology
Mice
Molecular Structure
Monosaccharides - chemical synthesis
Monosaccharides - chemistry
Monosaccharides - pharmacology
Oxidation-Reduction
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrroles - pharmacology
Pyrroloiminoquinones - chemical synthesis
Pyrroloiminoquinones - chemistry
Pyrroloiminoquinones - pharmacology
Stereoisomerism
Topoisomerase II Inhibitors
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Summary:An approach to the synthesis of the tetrahydropyrroloiminoquinone alkaloids has been developed and applied to the preparation of N-1-β-d-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization of aryl-methoxyamides by hypervalent iodine to construct the quinoline framework shared by members of this alkaloid family. The hypervalent iodine oxidant is generated in situ by anodic oxidation of iodobenzene.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902566p