A common approach to the total synthesis of L-arabino-, L-ribo-C-18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from D-mannose

作者：Martinkova Miroslava^*; Pomikalova Kvetoslava; Gonda Jozef; Vilkova Maria

来源：Tetrahedron, 2013, 69(38): 8228-8244.

DOI：10.1016/j.tet.2013.07.028

• Sphingolipids
• Phytosphingosine
• Jaspine B
• Rearrangements
• Trichloroacetamides
• Isothiocyanates

A common strategy for the total syntheses of the protected L-arabino- and L-ribo-Cm-phytosphingosine (8 and 9, respectively), HCl salts of ent-2-epi-jaspine B (ent-6) and 3-epi-jaspine B (7) with efficient use of both flexible building blocks 26 and 27 was achieved. The key step of this approach was [3,3]-sigmatropic rearrangement of allylic trichloroacetimidate 21 and thiocyanate 22, which were derived from the known 2,3:5,6-di-O-isopropylidene-D-mannofuranose 18 as the source of chirality. The side chain functionality was installed utilizing a Wittig reaction.

• 出版日期2013-9-23