Hello everyone, it's been a long while since I walked these hallowed halls, but I had an idea kind of spring itself upon me as I sat in the lab musing over a few synthetic papers...
http://rhodium.lycaeum.org/chemistry/it-290.html
As everyone knows, the above link is to the synthesis of AMT located on Rhodium's page. Being more interested in synthetic chemistry than it's personal use, I wondered about a synthesis starting from that ubiquitous material Tryptophan.
Ok, here's the plan...
1) Reduction of Tryptophan or it's ester by the usual routes i.e. LiAlH4 or BH3/THF.
2) Elimination of that pesky alcohol group to it's corresponding methyl which takes us to our finished compound.
Ok, the first part is relatively simple, but what about the second? You can't reduce the group using standard methods, so how about these two papers which have definitely graced the Hive before...
1) Olah, G.A. et. al., J. Org. Chem., 44(, 1979, pp 1247.
2) Sakai, T., et. al., Tet. Let., 28(33), 1987, pp 3817.
Both of these papers are different spins on Me3SiCl and NaI. The first turns the alcohol into a Iodide, and the second eliminates it all together. Both sets of reaction proceed at room temperature in good to excellant yield.
Three question therefore arise, 1) Can this chemistry be applied to indole containing system for the elimination of the slcohol, 2) what if any side-reactions may occur, and 3) if the iodide is isolated, what subsequent reaction can be used to eliminate that?
I leave these questions in your capable hands for further pondering...
Yours, as always...
Rhenium