Thursday, August 1, 2013

Scalable Ingenol? Phil Strikes Again!

Update: Want the inside scoop? Check out Open Flask!

I'm officially declaring it: Every 6-7 months, we should expect another huge molecule to fall to Phil & Co:

May 2011: Cortistatin
November 2011: Taxane Cores
May 2012: Ten Meroterpenoids.
December 2012: Ouabagenin

July 2013: Seen the latest* over at ScienceExpress? I think this scheme sums the whole thing up quite nicely:

And that's why it's in Science, kids...
Source: Baran Group | ScienceExpress
Ingenol falls! LEO Pharma, in collaboration with Scripps, may soon make gram-scale batches of ingenol analogs - something that used to take entire groups years to make. This paper cheers from so many different bleachers, I can't even count 'em all:

Total synthesis accesses trace plant metabolite!
Investment in basic research reaps huge Pharma dividends!
Imitating nature makes stitching together complex terpenes look easy!
Enzymes, Schmenzymes...

This paper really does have something for everyone. A volatile intermediate gumming up the works. A surprise crystallization. X-Ray structures. Some allenic Pauson-Khand reactions. A low-temp vinylogous pinacol rearrangement. Even some C-H activation / oxidation tossed in at the end.

If you want some more ingenol goodies, head on over to Chemistry World's fantastic write-up.
And, of course, join me on PhilWatch somewhere around January 2014...

*Thanks again to Brandon for a copy.


  1. i like the pictures they included in the SI

    1. Yes! Me too. Although I can imagine that since this route was patented, they couldn't really go the #realtimechem route :P

  2. This is very interesting for me: LEO is an ex-employer of mine, and Jakob Felding an ex-colleague from another Danish company. Go Denmark! :)

  3. I am disappointed that all of these blogs are cheer-leading for famous groups like Baran rather than critical analysis of the science. These guys are doing a great job over-promoting themselves with the help.