An Alternative Synthesis of 1,1′-Bis-valienamine from d-Glucose

An alternative synthesis of 1,1′-bis-valienamine 5, which was demonstrated to be a potent trehalase inhibitor, has been achieved from d-glucose in 12 steps with 15% overall yield via enone 12 as the key intermediate, involving a direct aldol reaction of a glucose-derived diketone and a palladium-cat...

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Veröffentlicht in:	Journal of organic chemistry 2010-05, Vol.75 (10), p.3522-3525
Hauptverfasser:	Shing, Tony K. M, Cheng, Hau M
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Cyclohexenes - chemical synthesis Cyclohexenes - chemistry Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Exact sciences and technology Glucose - chemistry Hexosamines - chemical synthesis Hexosamines - chemistry Molecular Conformation Organic chemistry Preparations and properties Stereoisomerism Trehalase - antagonists & inhibitors
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Beschreibung
Zusammenfassung:	An alternative synthesis of 1,1′-bis-valienamine 5, which was demonstrated to be a potent trehalase inhibitor, has been achieved from d-glucose in 12 steps with 15% overall yield via enone 12 as the key intermediate, involving a direct aldol reaction of a glucose-derived diketone and a palladium-catalyzed allylic coupling reaction as the key steps.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo100474p