What Happened to EJCorey.com?

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 ejcorey.guru or ejcorey.expert!)

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?

An "Ironic" Pauson-Khand

How would you go about making this compound?

(+)-ileabethoxazole

Taking a casual glance, I'd offer up at least a few disconnections. An epoxide-opening cascade, starting from that alcohol in the lower left hand corner. Maybe make the oxazole last, after some funky bismuth rearrangement chemistry. Perhaps you think you could stitch together the middle with some new-wave aryne technology?

Well, the Williams group (Indiana) took a completely different tack: a 9-iron. 

Not the reagent in question.

No, not the golf club, but di-iron nonacarbonyl. This dimeric "precatalyst" is thought to dissociate under the reaction conditions to Fe(CO)4, an unsaturated iron species that can complex to a variety of pi groups. It's been used for the Pauson-Khand for about 20 years, but the Williams group uncovered a new wrinkle last year: according to calculations, the iron might be initiating at the allene using a 3-membered metallacyclic ring! 

Very cool.  

Using these results, the Williams group mentally unzips the cyclopentane to this retrosynthetic intermediate (right). This wasn't the first thing they tried - that MOM ether on the oxazole came only after brominated versions of the heterocycle kept falling apart. Amazingly, the diiron complex ignores the alkyne, oxazole, and the MOM, choosing instead to complex to the end of the allene. Alkyne complexation, CO insertion, et voila! Cyclopentanone, coming right up (61% yield). Three more steps (deprotection, Swern, and base-promoted cyclization) produce the desired four-ring core.

The paper possesses blind alleys, full-stop restarts, theoretical underpinnings, and a good mission - anti-tuberculosis activity. Well worth reading the whole thing.

Science Blackout Poetry

Inspired by Austin Kleon and the New York Times, honoring National Poetry Month.

Update (April 27): A Reddit commenter (rightly) points out to also assign credit to Tom Phillips' Humument Project...good call!

JACS 2012, 11992

JACS 2014, 5257

JACS 1993, 9293

The Incredibly Consistent R.B. Woodward

Fans of the blog know of my playful hero-worship of R.B. Woodward. A man so well-known for both his chemical triumphs and signature eccentricities (blue suits, cigarettes, slow lectures) should expect nothing less.

Recently, the ACS Division of Organic Chemistry gave me good reason to go goof around on their newly-designed site. I became especially intrigued with their collection of old National Organic Symposium brochures. Among male contemporaries, only E.J. Corey spoke at more NOS meetings (8) than RBW (tied with six others at 6 apiece).

Check out my slow-mo time-lapse photography, culled from appearances in the NOS brochures:

First, E.J. Corey, over a 52-year NOS span:

Next, RBW, over 28 years:

Wow. Same suit, same glasses, same haircut, same expression, far as I can tell!

(He really favored that left side, huh?)

Check out the titles of Woodward's talks:

• 1977 - "Recent Advances in the Chemistry of Natural Products"
• 1967 - "Recent Advances in the Chemistry of Natural Products"
• 1957 - "Recent Advances in the Chemistry of Natural Products"
• 1953 - "Recent Advances in the Chemistry of Natural Products"
• 1949 - "Recent Studies on the Structure of Natural Products"

(P.S. All of E.J.'s talk titles were completely different!)

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.

Digging Nobel Data

The hot topic in the chemblogosphere this past week? The 2012 Nobel Prizes.

Just after the fervor had died down, Samuel Arbesman over at Wired wrote a piece about data mining the Nobel prize nominees. Well, there goes my weekend!

Sea Creature? Alien ship? Nope, just a light fixture.

See, the Nobel foundation (wisely) restricts release of the nominations until 50 years have passed. Thus, the data are somewhat dated, and they're not available online for all the prizes yet; sadly, Chemistry currently lacks any nomination data. But, ironically, a fully searchable database exists for Physiology and Medicine prize nominations, ca. 1900-1951.

Raw Hits - Playing around, I entered in terms one might choose for interdisciplinary awards: chem (235 hits), drug (only 7 hits!), crystal (54 hits), antibiotics (28 hits), and reaction (84 hits).

Usual Suspects - Future winners no doubt collect their share of early nominations, such as Waksman (streptomycin, 43 nods), Fleming (penicillin, 34 nods), and Ehrlich (chemotherapy / staining, 73 nods).

Superlatives - Obviously, the "career prize" aspect of the Nobel entered into judging quite early. Paul van Grutzen nominated Emil Abderhalden in 1917, saying "With great elegance [he] has solved many problems in chemistry." Two nominators in 1901 and 1905 nominated Albert von Koelliker for "A 60 year career in anatomy." In 1950, 10 nominators chose to "stuff" the ballot box in favor of Edward Kendall "...for his notable contributions to biochemistry."

Special Award Goes to...Prof. Jacques Loeb (UChicago / UC-Berkeley / Rockefeller). Far as I can tell, Dr. Loeb wins for most nominations in this category - 79 times, from 1901-1924 - without winning the Prize. His work involved artificial parthenogenesis, inducing egg cells to begin division without prior fertilization, using chemical signalling molecules and UV light.

Readers: Have fun with the database, and let me know what you find in the comments!