Synthesis of (2S,3R,11S,12R,2′R,11′S,12′R)-plakoside A, a prenylated and immunosuppressive marine galactosphingolipid with cyclopropane-containing alkyl chains

Plakoside A (1) is a prenylated galactosphingolipid isolated from the marine sponge Plakoartis simplex and is strongly immunosuppressive without cytotoxicity. (2S,3R,11S,12R,2'R,11'S, 12'''R)-plakoside A (1) was synthesized by combining sphingosine part 16, alpha -hydroxy acid part 24 and prenylated sugar part 29. (C) 2001 Elsevier Science Ltd. All rights reserved.