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High-Yielding Synthesis of Sphingoid-Type Bases

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journal contribution
posted on 18.09.2009, 00:00 by Catherine Séguin, Franck Ferreira, Candice Botuha, Fabrice Chemla, Alejandro Pérez-Luna
An efficient methodology for the synthesis of sphingoid-type bases is reported. It involves the stereoselective addition of a racemic 3-alkoxy allenylzinc to enantiopure N-tert-butylsulfinyl imines and a cross-metathesis reaction as the key steps. It has been successfully applied to the syntheses of sphinganine and naturally occurring bioactive related compounds, among which the hydrolysis product of clavaminol H and two spisulosines. All of these compounds have been prepared in six steps from N-tert-butylsulfinyl imines in high overall yields (>56%).