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.


  1. I like it, but are you sure you weren't influenced by my punning in this article about marine product syntheses that go *ahem* all the way up Halaven?

    1. Sad to say, but no, I hadn't seen that. Beautifully done, highly puntastic. I had to read it thrice to grok the funny. [bows respectfully]

  2. That paper is so saccharin it's unreadable

  3. A little heavy on the superlatives but its Taiwanese authors are probably ESL, and thus i give a little more slack. The editors could have taken it down a notch though.

  4. "Gratifyingly"... they had to use that too. It's the ultimate pat-on-your-back I see in chemical literature.

  5. Thanks for indelibly connecting natural product synthesis with This Is Spinal Tap. I will never think of the field the same again. Now I cant stop wondering what is the total synthesis equivalent of the 18" Stonehenge (New 24 step synthesis of salicylic acid?)