Friday, July 31, 2015

Friday Fun: Strained Conversation

This graphic was far too funny (to me, anyway) to leave buried in the graphical abstracts...

Courtesy of this Angewandte Chemie paper, in which we learn that "anti-Bredt" olefins - those C=C bonds located at the bridge of a caged bicyclic ring system - don't have to be discarded as possible structures for new natural products. The authors recommend their computational model, which uses modern forcefields to estimate olefin strain (OS) and predict stability of these bridgehead double bonds.

Happy Friday, everyone!
See Arr Oh

*I know this is a bit belated, but RIP P.v.R. Schleyer. You seemed like a really interesting guy.

Wednesday, July 29, 2015

"But...This Synthesis Goes Up to Eleven!"

Have you had fun reading through all the hilarious send-ups on the Twitter hashtag #HonestChemTitles? This tag tries to dig down to the subtext behind highfalutin words and strange symbols, uncovering the hidden motivations behind scientific papers.'s a hoot.

Remember the tweet that kicked off this brouhaha? A harmless convergent synthesis of some Lycopodium alkaloids. Kudos to @AlexFGoldberg for highlighting the authors' rather overblown title:

Classic children's literature;
my first exposure to superlatives
Amazingly, that 10-word title is 30% superlatives and 30% chemistry, with a smattering of conjunctions and articles to connect them. As others pointed out, how do you measure "elegantness," anyway? And when does a total synthesis cross the line from concise to exceedingly so; can anything more than a one-stepper be really succinct?

Sort through the paper with a grammarian's fine-toothed comb; one wonders if it wasn't run through some sort of excitement thesaurus, perhaps to get people really stoked about these routes.

Here's all the intense words and expressions I found:

Exceedingly concise and convergent

...and that's just in the first paragraph, folks.

Nigel Tufnel (Christopher Guest), ca. 1984
Honest opinion? Aside from the goofy title and superlatives liberally sprinkled into the text, the chemistry seems solid. Nothing's breathtaking - setting an early quaternary center through steric control is nice, and telescoping the three steps before the desired tetracyclic dione works well - but there's no "killer reaction" for me in this paper. The NMRs are clean, and the synthesis represents a decent improvement over existing methods.

Thus, I'd like to accept this publication into the "Spinal Tap Synthesis" category, so-named for the hard rock auteurs profiled in 1984's This is Spinal Tap, the tongue-in-cheek rock mockumentary. If you've never watched the movie, I won't spoil it, but I highly recommend the sequence in the middle where Nigel Tufnel, the vapid, misunderstood lead guitarist, obsesses over a "special" amp he designed that "goes to 11."

Fits this paper to a T.

Friday, July 17, 2015

Friday Potpourri: MegaMan, Lab Coats, More Worms

Please excuse my general lack of posting. When "Big Work Project" finally wraps, I'll have a bit more time for chemistry frivolity. In the meantime, how about a little collection of  almost-posts to help you into your weekend?


Faculty Fun: Maintaining a list of faculty moves can be tedious, but sometimes you find little gems on group pages. For example, Jeff Rinehart's group at UCSD will study magnetic materials. The logical mascot? A MegaMan master robot! (Vittorio would be so pleased...)


Last month, thought-provoking Chemistry World columnist Philip Ball wrote about white lab coats as badges of professional scientific stature. You may recall that one of my first posts here at JLC referred to the many ways in which such a white coat could be spoiled. I'm not exactly certain why - supplier availability, fire resistance, styling, cheaper? - but chemists in some younger synthetic organic chemistry groups seem to prefer blue lab coats.
Need evidence? Click below:

Phil Baran group
Stephenson group
Meek group
Shenvi group

(Readers: Know of more indigo-hued groups? Please mention in the comments)

Finally, for fans of vermisynthesis (who isn't?), you may notice that the chemblogosphere is giggling about this recent Tetrahedron paper on catalytic earthworms. Quintus points back to a 2014 PLoS One, but how far back have chemists truly considered the lowly earthworm as synthetic feedstock? Professor Leonardo Santos of the University of Talca, Chile, has investigated bioreduction of beta-carbolines since at least 2013. Perhaps he was inspired by the work of Kohji Ishihara, who published similar reductive behavior in cell-free worm extracts back in 2006. And both should potentially thank D.Q. Keiline, a reference in Ishihara's manuscript, who back in 1920 published "On the pharyngeal or salivary gland of the earthworm," which portended some of the proteolytic enzymes found therein.

Worm salivary glands ( in picture). You're welcome.
Source: Keiline, 1920

Tangentially, it's worth noting that an engineer in Colombia recently commercialized "biofilters" made of (living) earthworms, which clean organic solids from waste water. Seems someone should take a harder look at the potential catalytic goldmines wriggling underfoot.

Happy, squirmy Friday, everyone!
See Arr Oh

Thursday, July 9, 2015

What Happened to

A few years ago, folks on Twitter were helping me to collect a list of superlative chemistry authors - those in the rarefied air of hundreds to thousands of published scientific articles. At the time, I had counted Nobelist E.J. Corey's papers by visiting his personal website, linked from his Harvard emeritus faculty page

Curious, I returned there this week to view some of his recent research, and found this splash page:

1. Does this mean that the domain name is available?
(Checks - nope, someone has it, but GoDaddy will gladly sell you or!)

2. If you were the Harvard chemistry department, wouldn't you take steps to ensure that your emeriti had a guaranteed web presence? Prof. Dave Evans' fantastic site comes to mind.

Anyone have more information on when we can expect Prof. Corey's site to come back?