A stereocontrolled route to d-ribo-phytosphingosine and sphinganine from an achiral secondary homoallylic alcohol using Sharpless kinetic resolution

A facile and efficient enantioselective route for the synthesis of d-ribo-phytosphingosine (1a) and sphinganine (1b) has been developed employing commercially available and cheap starting material trans-cinnamaldehyde 2. The synthetic strategy features the Sharpless kinetic resolution, regioselective epoxide opening and Wittig olefination as the key steps.