Post 224070 (missing)
(megamole: "Re: route from acetaminophen (paracetamol)", Chemistry Discourse) says to tosylate the phenol, then reduce it away. Still, that's kind of drastic conditions. It's hard for me, at least, to trust indole compounds to stay robust in such harsh circumstances. You have to worry about attack at the 1-nitrogen, with complete delamination :( of your heterocycle, as well as what happens at the known sensitive 3-position. So while "impossible" may bee oversimplified, we can say for sure it's real impractical.http://www.garynull.com/Documents/spectrum/return_of_tryptophan.htm (http://www.garynull.com/Documents/spectrum/return_of_tryptophan.htm)
http://www.aclu.org/congress/issues107.html (http://www.aclu.org/congress/issues107.html)