A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylationElectronic supplementary information (ESI) available: 1H NMR, 13C NMR spectra of compounds 16, 18, 19, 20, 9, 23, 25, 26, 28, 10, 33-39, 12, X-ray crystallographic data, and the ORTEP diagram for compounds 27. CCDC reference number 773906. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c0ob00117a

• Main Authors: Kumar, Pradeep, Dubey, Abhishek, Puranik, Vedavati G
• Format: Journal Article
• Language: English
• Published: 27.10.2010
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c0ob00117a

A novel, practical and efficient enantioselective synthesis of sphingoid bases, l - threo -[2 S ,3 S ]-sphinganine (safingol), l - threo -[2 S ,3 S ]-sphingosine, l - arabino -[2 R ,3 S ,4 R ] and l - xylo -[2 R ,3 S ,4 S ]-C 18 -phytosphingosine is described. The synthetic strategy features the Sharpless kinetic resolution and tethered aminohydroxylation (TA) as the key steps. A novel, practical and efficient enantioselective synthesis of sphingoid bases, l - threo -[2 S ,3 S ]-sphinganine (safingol), l - threo -[2 S ,3 S ]-sphingosine, l - arabino -[2 R ,3 S ,4 R ] and l - xylo -[2 R ,3 S ,4 S ]-C 18 -phytosphingosine is described. The synthetic strategy features the Sharpless kinetic resolution and tethered aminohydroxylation as the key steps.