Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization

A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. Finally, various reduction conditions afforded the natural...

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Veröffentlicht in:	Organic & biomolecular chemistry 2012-08, Vol.10 (29), p.5541-5546
Hauptverfasser:	Gouault, Nicolas, Le Roch, Myriam, Pinto, Gisele de Campos, David, Michèle
Format:	Artikel
Sprache:	eng
Schlagworte:	Alanine Alanine - chemistry Alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry Biochemistry Biochemistry, Molecular Biology Catalysis Cyclization Gold Gold - chemistry Life Sciences Piperidines Piperidines - chemical synthesis Piperidines - chemistry Pyridones Pyridones - chemistry Stereoisomerism
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Zusammenfassung:	A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. Finally, various reduction conditions afforded the natural products in few steps and good overall yields.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/c2ob25685a