High-yielding synthesis of sphingoid-type bases.
作者： Catherine Séguin , Franck Ferreira , Candice Botuha , Fabrice Chemla , Alejandro Pérez-Luna
DOI: 10.1021/JO901567Q
关键词: Sulfonium Compounds 、 Hydrolysis 、 Organic chemistry 、 Enantiopure drug 、 Metathesis 、 Stereoisomerism 、 Chemical synthesis 、 Imine 、 Stereoselectivity 、 Chemistry
摘要: An efficient methodology for the synthesis of sphingoid-type bases is reported. It involves stereoselective addition a racemic 3-alkoxy allenylzinc to enantiopure N-tert-butylsulfinyl imines and cross-metathesis reaction as key steps. has been successfully applied syntheses sphinganine naturally occurring bioactive related compounds, among which hydrolysis product clavaminol H two spisulosines. All these compounds have prepared in six steps from high overall yields (>56%).
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