An efficient and stereoselective synthesis of (2R,2′S)-1-O-(2′-hydroxyhexadecyl)glycerol and its oxo analogs: Potential antitumour compounds from Shark Liver Oil

Article abstract of DOI:10.1016/0040-4020(96)00278-5

Reproducible, high-yielding, cost efficient, regio- and stereoselective synthesis of the title compound 3 isolated from Shark Liver Oil has been described. The compound 3 is prepared in an overall yield of 41% from chiral synthon 4 by the sequential reaction of 4 with C-13 Wittig salt; hydrogenation; epoxidation and regioselective opening. The oxo analogs 18 and 19 are prepared from four different achiral synthons by the sequential regioselective opening of the corresponding epoxide with different alcohols, methylation and deprotection strategies. Copyright