An efficient substitution reaction for the preparation of thyroid hormone analogues.
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.
Yoshihara
H A
HA
Department of Cellular and Molecular Pharmacology, University of California, San Francisco 94143-0450, USA.
Chiellini
G
G
Mitchison
T J
TJ
Scanlan
T S
TS
D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D011988:Receptors, Thyroid Hormone / Q000037:antagonists & inhibitors*; D013963:Thyroid Hormones / Q000138:chemical synthesis* / Q000737:chemistry; D014284:Triiodothyronine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D001577:Benzophenones; D008024:Ligands; D011988:Receptors, Thyroid Hormone; D013963:Thyroid Hormones; D014284:Triiodothyronine