Author/Authors :
van den Berg، نويسنده , , Richard J.B.H.N. and Korevaar، نويسنده , , Cornelis G.N. and van der Marel، نويسنده , , Gijsbert A. and Overkleeft، نويسنده , , Herman S. and van Boom، نويسنده , , Jacques H.، نويسنده ,
Abstract :
d-erythro-Sphingosine (1) and d-erythro-2-azidosphingosine (2) are both prepared from commercially available and cheap d-ribo-phytosphingosine (3) in a yield of 58% and 70%, respectively. A key transformation in the synthesis of d-erythro-sphingosine (1) is the palladium catalyzed regiospecific reduction of the Z-enol triflate 9. A crucial step in the synthesis of azidosphingosine 2 comprises a regio- and stereoselective in situ trans-elimination of the 4-O-triflate of azidophytosphingosine 13.
