Synthesis of carbamate derivatives containing anandamit unit

In this study, phenyl carbamate derivatives, which are thought to show biological activity and contain all cis-trien series such as anandamide, were synthesized. For this reason, in the first step methyl hex-5-ynoate was synthesized. In the second step, 4-chloro-but-2-yn-1-ol was synthesized. In the third step, methyl 10-hydroxydeca-5,8-diynoate was synthesized by reacting compounds which are synthesized in the first two steps. In the fourth step, methyl 10-hydroxydeca-5,8-diynoate was converted to methyl 10-bromodeca-5,8-diynoate by bromination. In the fifth step, methyl 14-hydroxytetradeca-5,8,11-triynoate was obtained by reacting methyl 10-hydroxydeca-5, 8-diynoate and but-3-yn-1-ol. In the sixth step, (5Z,8Z,11Z)-methyl 14-hydroxytetradeca-5,8,11-trienoate, which is our key component, was obtained from methyl 14-hydroxytetradeca-5,8,11-triynoate via hydrogenation. In the sixth step, (5Z,8Z,11Z)-methyl 14-hydroxytetradeca-5,8,11-trienoate, which is our key component, was obtained via hydrogenation of methyl 14-hydroxytetradeca-5,8,11-triynoate. In the other step, experiments were performed on alkylation reaction of (5Z,8Z,11Z)-methyl 14-iodotetradeca-5,8,11-trienoate, which was obtained by halogenating our key component with iodine, aniline and pyridin-3-amine.In the other step, methyl 14-((methylsulfonyl)oxy)tetradeca-5,8,11-triynoate was obtained by reacting methyl 14-hydroxytetradeca-5,8,11-triynoate and MsCl. Substitution reactions of methyl 14-((methylsulfonyl)oxy)tetradeca-5,8,11-triynoate, aniline and 2-aminophenol were analyzed. As a result of these experiments, the formation of methyl tetradeca-13-en-5,8,11-triynoate, which is the product of elimination instead of the product of substitution, was observed.At the last stage of this study, (5Z,8Z,11Z)-methyl 14-((phenylcarbamoyl)oxy)tetradeca-5,8,11-trienoate, (5Z,8Z,11Z)-methyl 14-(((4-chlorophenyl)carbamoyl)oxy)tetradeca-5,8,11-trienoate, (5Z,8Z,11Z)-methyl 14-(((3-chlorophenyl)carbamoyl)oxy)tetradeca-5,8,11-trienoate, (5Z,8Z,11Z)-methyl 14-((p-tolylcarbamoyl)oxy)tetradeca-5,8,11-trienoate, (5Z,8Z,11Z)-methyl 14-((o-tolylcarbamoyl)oxy)tetradeca-5,8,11-trienoate, (5Z,8Z,11Z)-methyl 14-(((4-bromophenyl)carbamoyl)oxy)tetradeca-5,8,11-trienoate and (5Z,8Z,11Z)-methyl 14-(((4-methoxyphenyl)carbamoyl)oxy)tetradeca-5,8,11-trienoate are obtained by reacting our key compound, (5Z,8Z,11Z)-metil 14-hidroksitetradeka-5,8,11-trienoat, with several phenylisocyanate derivatives in benzen and the presence of pyridine. The structures of the obtained compounds were determined by the spectroscopic methods (1H-NMR, 13C-NMR and FTIR).Key Words : All-cis-trienes, Anandamide anologs, Carbamate