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 Plakortis 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, α-hydroxy acid part 24 and prenylated sugar part 29.