Expedient entry to the piperazinohydroisoquinoline ring system using a sequential Ugi/Pictet-Spengler/reductive methylation reaction protocol

An expedient entry to the piperazinohydroisoquinoline ring system present in the tetrahydroisoquinoline antitumor alkaloids family is described. The synthetic sequence involves: a sequential Ugi reaction followed by an N-Boc-deprotection process and iminium formation with a spontaneous Pictet-Spengl...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2011-10, Vol.47 (38), p.10770-10772
Hauptverfasser:	Cano-Herrera, Ma-Angeles, Miranda, Luis D
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Crystallography, X-Ray Cyclization Isoquinolines - chemical synthesis Isoquinolines - chemistry Methylation Molecular Conformation Oxidation-Reduction Piperazines - chemistry Stereoisomerism
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Zusammenfassung:	An expedient entry to the piperazinohydroisoquinoline ring system present in the tetrahydroisoquinoline antitumor alkaloids family is described. The synthetic sequence involves: a sequential Ugi reaction followed by an N-Boc-deprotection process and iminium formation with a spontaneous Pictet-Spengler cyclization and reductive N-methylation, with all these processes performed in a two-operation protocol in the same reaction flask.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c1cc10759c