Tricyclic Alkaloid Core Structures Assembled by a Cyclotrimerization−Coupled Intramolecular Nucleophilic Substitution Reaction

Tricyclic Alkaloid Core Structures Assembled by a Cyclotrimerization−Coupled Intramolecular Nucleophilic Substitution Reaction

A facile approach to tricyclic alkaloid core structures was developed by sequencing a pyridine-forming [2 + 2 + 2] cyclotrimerization reaction with an intramolecular nucleophilic substitution. This methodology enabled the facile assembly of the spiroindolinone framework of citrinadins A and B, and c...

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Veröffentlicht in:Organic letters 2010-03, Vol.12 (6), p.1288-1291
Hauptverfasser: McIver, Andrew L, Deiters, Alexander
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Cyclization
Microwaves
Molecular Structure
Pyridines - chemistry
Stereoisomerism
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Zusammenfassung:A facile approach to tricyclic alkaloid core structures was developed by sequencing a pyridine-forming [2 + 2 + 2] cyclotrimerization reaction with an intramolecular nucleophilic substitution. This methodology enabled the facile assembly of the spiroindolinone framework of citrinadins A and B, and cyclopiamine B.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100177u