Iodine(III)-Mediated Generation of Nitrogen-Tethered Orthoquinol Acetates for the Construction of Oxygenated Indole, Quinoline, and Phenanthridine Alkaloid Motifs

Functionalized indole and quinoline derivatives are conveniently prepared from nitrogen-tethered 2-methoxyphenols via phenyliodine(III) diacetate mediated oxidative acetoxylation, followed by a fluoride- or base-induced intramolecular nucleophilic addition reaction. This regioselective Michael-type...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-05, Vol.67 (10), p.3425-3436
Main Authors: Pouységu, Laurent, Avellan, Anne-Virginie, Quideau, Stéphane
Format: Article
Language:English
Subjects:
Acetates - chemistry
Alkaloids - chemical synthesis
Alkaloids - chemistry
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Hydroquinones - chemistry
Indoles - chemical synthesis
Iodine - chemistry
Molecular Structure
Nitrogen Compounds - chemical synthesis
Organic chemistry
Preparations and properties
Quinolines - chemical synthesis
Temperature
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Summary:Functionalized indole and quinoline derivatives are conveniently prepared from nitrogen-tethered 2-methoxyphenols via phenyliodine(III) diacetate mediated oxidative acetoxylation, followed by a fluoride- or base-induced intramolecular nucleophilic addition reaction. This regioselective Michael-type addition step is further discussed in view of the rearrangement of orthoquinol acetate intermediates into paraquinol acetates that is sometimes observed in situ. Application of this methodology to the synthesis of a functionalized phenanthridine, and its potential for the construction of polyoxygenated lycorine-type alkaloid skeleta are here described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020010d