"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. And...it'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:

Diverse
Useful
Unique
Challenging
Efficient
Complete
Direct
Achieved
Accomplished
Value
Exceedingly concise and convergent
Attractive

...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 Fun - Superlative Publishers

Who's got the highest total # of published papers among living synthetic chemists?

Criteria: The person runs a group that makes things - sorry, no theorists this round - and works principally in some sub-field of synthetic chemistry (organic, organometallic, inorganic, photochem, med-chem, polymers, etc). 

I opened the discussion up on Twitter this morning, and used SciFinder, backed up with [cough] group websites that often need updating [cough]. 

Here's the list, as of 10:00 CST...

(All counts rounded to nearest 100 for convenience. SciFinder is an imperfect metric, since it includes abstracts and some duplicate entries. Please refer to caveats, below, for more detail.)

Alan Katritzky: 2,200 website; 2600 SciFinder

Source: exchangewire.com

Robert S. Langer: 2000 SciFinder

George Whitesides: 1,200 website; 1900 SciFinder

Leo Paquette: 1500 SciFinder

*E. J. Corey: 1,000 website; 1500 SciFinder

J. Fraser Stoddart: 1,000 website; 1400 SciFinder
Tobin J. Marks: 1,000 website, 1600 SciFinder
Paul v. Rague Schleyer: 1,300 website; 1600 SciFinder
Jean Frechet: 800 website; 1300 SciFinder
Irina Beletskaya: 1300 SciFinder

Barry Trost: 900 website; 1200 SciFinder

K.C. Nicolaou: 700 website; 1200 SciFinder

D. Reinhoudt: 1200 SciFinder

J. S. Yadav: 1,000 website; 1200 SciFinder

Ben Feringa: 1100 SciFinder
J-M. Lehn: 1100 SciFinder

E.W. "Bert" Meijer: 1000 SciFinder

Robert "Bob" Grubbs: 1000 SciFinder
Virgil Percec: 1000 SciFinder

Samuel "Sam" Danishefsky: 700 website; 1000 SciFinder

Ryoji Noyori: 800 SciFinder

Steven Ley: 900 SciFinder
Amos B. Smith: 900 SciFinder
James Tour: 500 website; 900 SciFinder
Stuart Scheiber: 500 website; 800 SciFinder
Karen Wooley: 700 SciFinder

Peter Langer: 700 SciFinder
Carolyn Bertozzi: 700 SciFinder
Jean'ne M. Shreeve: 500 website; 700 SciFinder
JoAnn Stubbe: 600 SciFinder

John Hartwig: 300 website; 600 SciFinder

K. Barry Sharpless: 600 SciFinder
Jacqueline Barton: 300 website; 600 SciFinder
Gautam Desiraju: 500 SciFinder
J.K.M. Sanders: 500 SciFinder

Ted Taylor: 500 SciFinder
Laura Kiessling: 400 SciFinder
M. Joullie: 400 SciFinder
Cynthia Burrows: 300 SciFinder
Melanie Sanford: 200 SciFinder

(Update: 1PM - Added Tobin Marks, Virgil Percec. 6PM - Added top-author women chemists. 7PM - Added Frechet, Desiraju, Sanders. 12AM 6/1 - Added Shreeve, Beletskaya)

Some caveats: I know it's folly to attempt correlating total publication count : scientific 'genius.'

If you only publish one paper, but you cure a major disease or invent a top-selling polymer additive, you're doing just fine! 

Also, I note that not everyone agrees that folks on this list belong in the "synthetic chemist" bucket - see ScienceGeist's (noted) exceptions here. (Update: P-O. Norrby noted another exception...)

Importantly, graduate students shouldn't feel down and out about this list. You can have a perfectly fine career with just a handful of papers; these superstars are the exception rather than the rule.

Curious thought: Publications in large synthetic groups certainly seem to follow a power law** - it takes ~15 years to get those first 100 papers, then about 8 for 100 more, and then the pace picks up dramatically. Presumably, this represents added hands and minds, along with building respect and excitement for one's work. I don't know how many other factors (prizes, location, grants, "buzz") are involved, but they probably belong to another post.

Readers, what say you? Have another person I've missed on the list?

*Who knew E.J. pwned ejcorey.com? (show of hands?) I think I smell a fantastic cyber-squatting campaign ...danishefsky.com, anyone?

**An example we discussed on Twitter: Phil Baran. It took him 15 yrs (1997-2011) to get 100 pubs. Next 25 or so have only taken 2 yrs. If power law holds, he'll have >400 pubs by age 50.

Superlatives: Kings of Polyene Mountain

(Thanks to BRSM, for unwittingly providing the theme for this post...)

"We can rebuild him...Better, stronger, faster..." - opening to Six Million Dollar Man

Today's society steeps in superlatives. Never content with the ordinary, we want to know who's the richest, fastest, and the best-looking. Our obsession with "most" even extends into our scientific publishing; JACS actively discourages words such as "novel" or "first" from its article titles.

Well, this paper must have slipped into the system unchecked. Behold: longest of the polyenes!

Martinez, Sliwka Org. Lett 2012

(That numbering system means 80 total carbons, and 27 bonds in conjugation. For example, butadiene is C4:2)

Why embark on this synthesis, to chase the olefinic "holy grail?" Three reasons: the pursuit of "lambda ultimate" (how far can we go into the red?), to fix errors in calculated specs (off by 104 nm!), and to create ever-longer molecular wires.

Check out the Supporting Info for an historical polyene primer, from 1899 to the present. Interestingly, the field seems to have run into roadblocks based not just on available synthetic methods, but on the rock-like solubility of many polyaromatics; further frustration stems from the instability of certain cyclic compounds I'm sure would like to Alder all over the place!

My favorite part of this saga? The gorgeous superstructure of the modeled C80:27 polyene.

Martinez, Sliwka Org. Lett 2012

You might expect an all-trans structure to be stiff as a board, but let's think conformationally - each "prenyl" unit has a methyl group bashing up 'A(1,3)-like' against a neighboring hydrogen. To avoid this, it twists and shifts, producing a pleasing undulation in the overall chain.

All kidding aside, the 'longest' title surely won't stand. Now that the authors have improved methods to synthesize soluble, all-trans, long-chain poly-olefins, it's a matter of time before something wild like C220:50 comes out.

Might I suggest "The Longest Polyene...For Now?"