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

Thiana S. Nascimento, Luciana G. Monteiro, Esther F. Braga, William R. Batista, André L. M. Albert, Leticia G. F. Chantre, Sergio de P. Machado, Rosangela S. C. Lopes, Claudio C. Lopes

Antifouling paints, Ethers lipids, Marine biofouling, Synthesis.

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.

10.22161/ijaers.5.5.43