A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation?

Organic & Biomolecular Chemistry Pub Date: 2010-09-15 DOI: 10.1039/C0OB00117A

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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