Synthesis of natural ether lipids and 1-O-hexadecylglycero-arylboronates via an epoxide-ring opening approach: Potential antifouling additives to marine paint coatings

In this paper a new and efficient procedure for the synthesis of natural 1-O- alkyl glyceryl ethers such as chimyl (1), batyl (2) and selachyl (3) is described. Alkyl glycidyl ethers (4-6) were synthetized using solvents free reactions. A stereospecific ring-opening reaction of epoxides (4-6) with phenylboronic acid in dry dioxane, giving rise to cyclic arylboronates in high yields (90-98%). Seven new 1-O-hexadecylglycero-arylboronates (7-f) and chimyl alcohol (1) were evaluated in laboratory antifouling assays.