Efficient and stereoselective syntheses of DAB-1 and d-fagomine via chiral 1,3-oxazine

The concise, stereocontrolled syntheses of DAB-1 and d-fagomine were achieved utilizing chiral oxazine. The key features in these strategies are the stereoselective intramolecular oxazine formation catalyzed by palladium(0), and pyrrolidine and piperidine formation by catalytic hydrogenation of oxaz...

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Veröffentlicht in:	Tetrahedron 2011-12, Vol.67 (48), p.9426-9432
Hauptverfasser:	Kim, Ji-Yeon, Mu, Yu, Jin, Xiangdan, Park, Seok-Hwi, Pham, Van-Thoai, Song, Dong-Keun, Lee, Kee-Young, Ham, Won-Hun
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Catalysis Catalysts Catalytic hydrogenation Chemistry d-Fagomine DAB-1 Exact sciences and technology Formations Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with only one n hetero atom and condensed derivatives Hydrogenation Natural product Organic chemistry Oxazine Pd catalyst Piperidine Preparations and properties Strategy Tetrahedrons
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Zusammenfassung:	The concise, stereocontrolled syntheses of DAB-1 and d-fagomine were achieved utilizing chiral oxazine. The key features in these strategies are the stereoselective intramolecular oxazine formation catalyzed by palladium(0), and pyrrolidine and piperidine formation by catalytic hydrogenation of oxazine. [Display omitted]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2011.09.084