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Issue 22, 2010
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A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation

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Abstract

A novel, practical and efficient enantioselective synthesis of sphingoid bases, L-threo-[2S,3S]-sphinganine (safingol), L-threo-[2S,3S]-sphingosine, L-arabino-[2R,3S,4R] and L-xylo-[2R,3S,4S]-C18-phytosphingosine is described. The synthetic strategy features the Sharpless kinetic resolution and tethered aminohydroxylation (TA) as the key steps.

Graphical abstract: A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation

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Publication details

The article was received on 13 May 2010, accepted on 21 Jul 2010 and first published on 15 Sep 2010


Article type: Paper
DOI: 10.1039/C0OB00117A
Citation: Org. Biomol. Chem., 2010,8, 5074-5086
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    A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation

    P. Kumar, A. Dubey and V. G. Puranik, Org. Biomol. Chem., 2010, 8, 5074
    DOI: 10.1039/C0OB00117A

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