Stereoselective total synthesis of (2R,2′S,3Z)-1-O-(2-methoxyhexadecenyl) glycerol and (2R,2′S)-1-(2′-methoxyhexadecyl)glycerol-potential antitumour compounds from Shark liver oil

Article abstract of DOI:10.1016/0040-4020(95)00156-3

A simple and high yielding route for the stereoselective synthesis of alkyl glycerol ethers namely (2R,2′S,3Z)-1-O-(2-methoxyhexadecenyl)glycerol 1 and (2R,2′S)-1-(2′-methoxyhexadecyl) glycerol 2, isolated form Shark liver oil is reported. The key reaction involves the Wittig olefination of the chiral aldehyde 12 with the ylide generated from tridecyl triphenyl phosphonium bromide results in the formation of compound 13, a precursor for the title compounds 1 and 2.