an extra OH on tyrosine

[methwerx]

Any leads on getting an extra OH on tyrosine in the 3 position?? Or even getting it there on 4 OH amphetamine. It seems that such a thing would bust the benzene ring (to me that is). And before someone posts it, a halogenation followed by hydroxylation (with NaOH) doesnt work on aromatics. It would be nice to make some progress here, as I think the Kolbe works pretty good on phenylalanine, an extra OH on tyrosine, followed by bridging the OH's with a MeX2 would be beautiful.
tip of the month: slugs in your bathroom keep the mould of the grout.

[Rhodium]

Check out the mmdamesc.txt on my page. It shows how to react an aryl bromide with hydroxide in the presence of copper to form the phenol. You would need to protect the nitrogen before doing this reaction on any nitrogenous substrate however I believe.