Synthesis Of Thyronine Analogues Thyronamine

Thyronamine are iodinational decarboxylational analogues of thyroid hormone. They show poor activation in the rat antigoitor experiments. In recent, researchers found they can bind trace amine receptor 1(TAR1), produced reverse biological activity of TR.In this thesis thyronamine analogues T₂AM, T₃AM and T₄AM were synthesized. The key step for the synthesis is copper-promoted O-arylation of arylboronic acids with phenols for the construction of novel aryl-O-aryl structures. T₂AM was prepared in 7 steps with 36.2% total yield, T₃AM, and T₄AM were prepared in 8 steps with an over yield of 38.1%, 27.5% successively. This work was of great importance for further studies on this kind of iodothyroid hormones analogues.