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May 15, 2007
Into The Trackless Wilderness
I had an e-mail the other day from a reader who pointed out that when anyone tells you something is simple or obvious in indole chemistry, that you should run for cover. He expressed similar worries about amino acids, and I take his point. There are some areas of organic chemistry that have huge encrustations of literature all over them, which can be a warning sign.
One way you get a literature jungle is for few general methods to work. That's always been my impression of indole chemistry - each reaction has its limited area of jurisdiction, but if you start messing around you find yourself in the lawless borderlands pretty quickly. I did my PhD work using carbohydrates for natural product synthesis, and I have to say that they've got the same problem. All kinds of interesting, funky things start happening when you do something so (apparently) innocent as using a galactose scaffold instead of glucose.
Of course, there's another way to pile up a lot of different reactions, which is for most all of them to work, more or less. I think that's been the situation for many years in the palladium-catalyzed reaction field. As I've said before, I believe that just about any Pd coupling can be made to work, if you're willing to devote enough of your life to tweaking the conditions. Can you imagine a comprehensive review of some of these reactions? You'd need a special nine-volume run of Organic Reactions to even have a hope, and where would you find the maniacs to write it all?
Readers are invited to submit other examples of literature swamps - another one I can think of, from the old days, are all those steroid transformations. But I know that there are others lurking out there. . .
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