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An efficient substitution reaction for the preparation of thyroid hormone analogues
H A Yoshihara1, G Chiellini, T J Mitchison
1Department of Cellular and Molecular Pharmacology, University of California, San Francisco 94143-0450, USA.
Bioorganic & Medicinal Chemistry
|October 24, 1998
Abstract:
The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich aromatic compounds, providing a convenient route to the synthesis of new thyroid hormone analogues.