Total Synthesis of the Biphenyl Alkaloid (−)‐Lythranidine

Autor:	Konrad Gebauer, Alois Fürstner
Rok vydání:	2014
Předmět:	Molecular Structure Total synthesis Cycloalkyne General Medicine General Chemistry Propargyl alcohol Metathesis Ruthenium Catalysis chemistry.chemical_compound Alkaloids Acetylene chemistry Alkyne metathesis Organic chemistry Oxidation-Reduction Isomerization Derivative (chemistry)
Zdroj:	Angewandte Chemie International Edition. 53:6393-6396
ISSN:	1521-3773 1433-7851
DOI:	10.1002/anie.201402550
Popis:	A sequence comprising a ring-closing alkyne metathesis of a propargyl alcohol derivative, followed by a ruthenium-catalyzed redox isomerization of the derived cycloalkyne and a transannular aza-Michael addition allowed the formation of the distinguishing piperidine-metacyclophane framework of the Lythraceum alkaloid lythanidine in a few high-yielding steps. This application attests to the excellent functional-group tolerance of a molybdenum alkylidyne complex endowed with triphenylsilanolate ligands, which enabled the macrocyclization even in the presence of protic functionalities, and thus illustrates the power of contemporary catalytic acetylene chemistry for target-oriented synthesis.
Databáze:	OpenAIRE
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