WWWTP? "Third-Party" Edition

Source: Kishida Chemical

A blog buddy sent along this puckish reminder of customer perception in the crowded chemical sourcing market. Seems Oakwood Chemical, a U.S.-based supplier, recently partnered with Kishida, a Japanese fine chemicals company.

Kishida specializes in med-chem building blocks, but seems to have a problem with their structure-drawing program (right)...where did all the hydrogens go? Don't think it's just on the website - the catalog goes 50/50 for abnormal heteroatom saturation.*

Readers, am I missing something (other than those "H" atoms)? Is this part of some common fragment representation, or is it just lazy drawing?

Comments welcome.

*For a good time, check cyclobutylhydrazine dihydrochloride (PK0-13441), which seems to be missing a record five (5) hydrogens! Can anyone top that?

Head-Scratching "Sanros" Structures

It's like a crossword puzzle...
Source: Chemistry World

Over at Chemistry World, Duncan Browne posted a review of a new applet version of the Kurti / Czako book Strategic Applications of Named Reactions in Organic Synthesis (for the hip iPhone crowd, the title has been condensed to simply "Sanros"). The trial version allows access to 25 out of the 250 reactions included in paid access. I'm all for chemistry-enabled free software making its way out into the public.

Just one tiny problem: what the heck is that structure? Maybe the atoms were inadverently deleted in transit, or perhaps it's meant as an artistic statement? I can't imagine this molecular graphic falls under Elsevier copyright protection.

In a way, it's like a detective mystery: can you infer what's missing? I took a crack at it myself (see below). I figured the structure on the right was either a dithiane (S,S) or ketal (O,O). The bottom ring could have any combination of N,O,S, so we'll swap in a morpholine. The aromatic? Gotta be a pyridine. Uh-oh, there could be anything terminating those 'short' bonds on the cyclopentane, or on the alpha bonds stemming below the cyclopropane. I'll just infer methyl groups, for now.

Of course, without knowing the actual natural product, and without access to database software due to the holiday, I have no way to know if I'm barking up the right tree. Anyone care to help?


Happy Fourth of July, everyone!


Update, 7/4/12 - Commenter @azmanam wins the platinum coin for his search efforts, locating the correct intermediate from a Boger total synthesis (see below). So, in the end, I went 4 for 9 on "mystery atoms!"

Stock Photo Fun - "Confused Scientist"

"Confused Scientist" (I can think of reasons why...)
Source: Royalty-Free Stock Photos

While searching for some stock photos to accompany an upcoming post, I found this gem. It's actually titled "Confused Scientist."

Well, let's start from the top, shall we?

- I've never seen anything labeled "Schematic Benzene Complex."

- I can't seem to draw a stable-looking, neutral compound from the formula she's considering. Five degrees of unsaturation, maybe a catechol or something? Anyone? Bueller? Bueller?

- You shouldn't eat chalk. Do you know where that's been?!?!

- Staring intently at the wall won't avail you. (ask Azmanam)

- The structure she's drawing, in addition to not having a benzene ring, just has valence errors jumping out from every which way. I count at least three.

Needless to say, I didn't opt to use this for my post. For more structure fun, check out ChemBark's WWWTP posts.

Memes and Bandwagons

I'm interested in how internet memes get started; it's probably the same mob psychology that drives events like Black Friday or stock market bubbles. Either way, when I read Carmen Drahl's Haystack post with the handwritten chemical structures, followed by Chemjobber's homage, I felt the urgent need to actively participate in what is, undoubtedly, the next big thing on the internet: structure drawing!!!



Perhaps I should link this to a catchy jingle, or a flashing banner ad?

 So, there you go, now I'm part of the groundswell. Feel free to comment or critique, I'll even start you off: yes, I know my hydrogens look like "4's", and the persnickety demands of my postdoc advisor for exactness drove my desire to cap off those alkyl stereocenters with an actual group. 

'Til we all meet again on YouTube, 14,000,000 hits later...