Buried Treasure

Regular readers know that I've been collecting names of chemistry faculty moves for a while now. I had to chuckle at this particular announcement, by friend of the blog (and fellow Tweeter) Prof. Karl Gademann. From two clicks deep on his group's home page:

"Prof. Gademann's first professorial appointment was at the EPFL in Lausanne, and he currently holds a chair at the University of Basel as a full professor. He has been elected to the board of the Swiss Academy of Sciences, and is affiliated to the National Centres of Competence in Research ‘Chemical Biology’ and ‘Molecular Systems Engineering’. Karl Gademann will move in Summer 2015 to the University of Zürich. His work has been recognized by a number of international awards, including the Latsis prize, the Novartis Early Career Award, the Ruzicka Medal, The Liebig Lecture by the German Chemical Society, and the European Young Investigator Award."

Thanks to an eagle-eyed commenter for the link.

Also, from both sites (UZH, BAS), it would appear that Dr. Gademann looks most professional when posed behind a rotovap condenser.

Best of luck in the new position, Karl - we'll add you to the list!

Acc. Chem. Res. = Suddenly Cool Again

Accounts of Chemical Research - located at the "left of your ACS radio dial"- may be as unloved as the random college radio stations one finds there. Yet it somehow seems to be catching fire with the chemistry "It" crowd.

Seriously...it's on the left!

I'd heard plenty of knocks back in grad school: "Self-reviews." "Citation fluffing." But, know what? I can't help but want to read most of these recent papers.

Take the upcoming Special Issue organized by Paul Wender. Entitled "Synthesis, Design and Molecular Function," it offers plenty of pizzazz. There's...

• Tom Hudlicky, whose "...20 years of effort [in synthesizing morphinans]...may qualify as obssession." 
• Karl Gademann "...unlocking secrets enshrined in molecular structure" towards neuroengineering.
• Brian Stoltz wants to show you "effective and broadly general methods for the formation of quaternary stereocenters."
• Phil Baran wants students "...to face challenges from the 'real world' at an early stage of their career"
• Frank Glorius wishes chemists would realize "...the value of negative and qualitative data" in reaction screening
• Glenn Micalizio advances "...an area of chemical reactivity not represented in the few well-established [C-C bond-forming] strategies" namely, metallacycles.
• Sam Danishefsky and Chi-Huey Wong tackle cancer vaccines. Need I say more?
• And Vinca alkaloids stalwart Dale Boger dives into vinblastine analogues.

I'm sure more will find their way onto the ASAPs, but this is an illustrious way to start the next issue.
Bravo, editors!

Let the Sun Shine In

Have you ever wondered why so many chemicals are shipped in amber-tinted bottles? Turns out light can do some pretty sneaky unexpected chemistry.

Reporting in from scenic Switzerland, Gademann & Co recently disclosed a sweet protecting-group free synthesis of Taiwaniaquinol F, a 6-5-6 diterpenoid with "potent cytotoxicity" against certain cancer cell lines. They finish the target in 17 steps, highlighting a Wolff ring-contraction and a neato halogen-oxygen exchange. 

The authors note that the final isolation had to strictly exclude light, or else their product slowly decomposed. Luckily, they asked themselves "Decomposed...to what?"

Source: Org. Lett. ASAP | Gademann group

Not to keep you in the dark; their product underwent a spontaneous 1,5 C-H remote functionalization. When the group tried to do it "on purpose" - placing a flask in the sun for 15 minutes - they were rewarded with a 30% yield of cyclized Taiwaniaquinol A.

The authors aren't quite sure what's so special about this system, but note a tantalizing biosynthetic possibility: since Taiwaniaquinol F comes from the bark of a certain tree, and "A" from its leaves, there's a real possibility that this process happens all the time in the plant! No enzymes, no metals, no bases. Just sunshine. 

Nature's amazing.