Enantioselective Formal Synthesis of Nectrisine Using a Palladium-Catalyzed Asymmetric Allylic Amination and Cross-Metathesis as Key Steps

A formal enantioselective synthesis of nectrisine, a potent α-glucosidase inhibitor, was carried out starting from butadiene monoepoxide through a synthetic sequence involving enantioselective allylic substitution, cross-metathesis, dihydroxylation, and cyclization.

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Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2016-06, Vol.81 (12), p.5217-5221
Hauptverfasser:	Soriano, Sébastien, Azzouz, Mariam, Llaveria, Josep, Marcé, Patricia, Matheu, M. Isabel, Díaz, Yolanda, Castillón, Sergio
Format:	Artikel
Sprache:	eng
Schlagworte:	Amination Amines - chemical synthesis Butadienes Catalysis Cyclization Glycoside Hydrolase Inhibitors - chemical synthesis Hydroxylation Imino Furanoses - chemical synthesis Indicators and Reagents Magnetic Resonance Spectroscopy Palladium - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	A formal enantioselective synthesis of nectrisine, a potent α-glucosidase inhibitor, was carried out starting from butadiene monoepoxide through a synthetic sequence involving enantioselective allylic substitution, cross-metathesis, dihydroxylation, and cyclization.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/acs.joc.6b00494