Synthetic edge

We had Silas Cook (Indiana University) visit our department earlier this week. This occasion presented an opportunity to learn about both his iron catalysis and total synthesis efforts. Silas’s imaginative route to artemisinin appeared in JACS several years ago and it remains a landmark of synthetic efficiency. You can see the paper in its entirety if you follow the link below, so I am just going to comment on one step – the Wacker oxidation to generate the ketone precursor. The reaction was done on a 9.4g scale. The search for the optimal condition had attracted my attention. Everything else went fairly miserable, but the hydrogen peroxide-mediated version of the Wacker process delivered the product with good yield. I appreciated hearing this story, particularly during the week when we heard about the Medicine Nobel Prize for the discoveries of artemisinin and ivermectin. As you may also know, Jay Kiessling of UC Berkeley has received a ton of attention (and tens of millions of dollars worth of funding) for his synthetic biology effort to find a production route to artemisinin, yet the jury is still out in regards to the economics of that method. Silas, on the other hand, is offering something really reasonable and inexpensive. My vote is with his synthesis.

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http://pubs.acs.org/doi/abs/10.1021/ja3061479

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