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October 10, 2013
Unpacking a JACS Total Synthesis Paper
If you're in the mood for some truly 100-proof synthetic organic chemistry, this post from Mark Peczuh at UConn is going to be just what you need. He's going through the 2002 synthesis of ingenol from the Winkler group, line by line, in an effort to show his own students how to read such highly compressed reports. Here's a bit of it, to give you the idea:
Paragraph 7: The payment for using 6 in place of 5 has come due. In paragraph 7, the authors quickly move through a series of transformations that convert 16 to 22. The key player that enables these transformations is the hydroxymethyl group attached to C6. Oxidation of that group to the corresponding aldehyde allows sequential eliminations that create the diene in 22. The authors report flatly in this paragraph that the seven steps reported are “to introduce the A ring functionality present in ingenol”. They don’t put emphasis on it, but it’s logical to think that they’d have preferred to carry an oxygenated C3 up to this point and done only one or two steps to be in a much better position than they presently are. So it goes.
That is indeed exactly the sort of thinking that you have to do to follow one of these things, and it definitely requires time and effort. This chemistry is the sort of work that I don't do (and have, in fact, questioned the utility of), but there's no doubt that it's an extreme intellectual and practical challenge, which this view can really make you appreciate.
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