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Derek Lowe The 2002 Model

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Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: Twitter: Dereklowe

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April 26, 2011

Graphical Crankiness

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Posted by Derek

And now a brief note from the "trivial but annoying" department, since it's been a couple of years since I last complained about this. Is there any way that we can start a petition, or take up a collection, or do something to make K. C. Nicolaou stop drawing ring systems like this? Coloring the insides of them with gradient fills adds no information and actually obscures elements of the structure.

If all else fails, can we at least send the man a set of Ed Tufte books?

Comments (67) + TrackBacks (0) | Category: The Scientific Literature


1. Happy Dog on April 26, 2011 9:29 AM writes...


For that matter, could we make the Tufte books required reading for all of pharma management?

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2. Keith Robison on April 26, 2011 9:35 AM writes...

While you are at it, the worst offenders in generating horrific graphics are the people whose only job is to do them.

Editors at all the major journals as well -- graphic techniques that distort the data (perspective pie charts being the worst, but not sole, villian) or remove useful comparisons pollute Science, Nature, Cell and the rest. The fact that tools such as PowerPoint and Excel encourage such rot isn't an excuse to use them.

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3. molecular architect on April 26, 2011 10:00 AM writes...

Amen! I can't stand KC's graphic foolishness. His books are full of this nonsense and now it's polluting the journals. Enough!

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4. KC Nicolaou on April 26, 2011 10:03 AM writes...

You're all jealous!

It's beautiful, like the Red Tide!

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5. See Arr Oh on April 26, 2011 10:13 AM writes...

Once upon a time, I saw lectures from KC and his prodigy Phil Baran in the same year. Between the two, the presentations are a graphical orgy of black backgrounds, neon writing and colored rings. Makes your eyes bug out by the end.

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6. InfMP on April 26, 2011 10:20 AM writes...

It serves its purpose. Everytime people are scrolling through the ASAPs, we know right away when KCN's got a new paper.
I gotta say I prefer the orange rings from Molecules that change the world and rather than the red on blue that he's been doing lately.

And what about Frank Glorius? Is it ok what he is doing because the colors are less intense?

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7. LeeH on April 26, 2011 10:23 AM writes...

I agree completely with your point, but Ed Tufte might not be the best example of how to do it concisely. K.C. may start to put in graphs of how many grad students it took to do the work, how many grants, etc... alongside the structures. Or size the arrows according to the yields.

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8. Vader on April 26, 2011 10:32 AM writes...


It makes perfectly respectable ring structures look a little like the Star Trek fictional giant amoeba creatures that attacked Spock on Deneva and nearly turned him into a raging madman.

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9. ag on April 26, 2011 10:40 AM writes...

What's more appalling - the ring coloring, or the fact that he published progress-toward in Angewandte?

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10. cynic on April 26, 2011 10:48 AM writes...

Well, nobody has pointed out yet that the functionalisation is all in the wrong place, so I guess it did a pretty good job of distracting us.

And while we're at it, let's keep words like 'exquisite' out of the damn abstract. Let the readers be the judge of that.

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11. anon 1 on April 26, 2011 11:07 AM writes...

Got your attention, eh?

Isn't this up to the journal, if the structural representaion is consistent with their guidelines?

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12. MTK on April 26, 2011 11:32 AM writes...

Attention-whoring at its finest. Indicates someone who needs to be noticed at all costs. Not unlike a graffiti artist with a distinctive style.

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13. Mowgli on April 26, 2011 11:40 AM writes...

Who knew Vader was a Trekkie? :)

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14. Anonymous on April 26, 2011 12:00 PM writes...

Most of these comments appear trivial and annoying to me, as this blog used to be inspiring and interesting ! Even if one wouldn't like the way the representations are coloured, then it still serves the purpose of highlighting the number of interconnected rings at a single glance - which also actually helps to overlook the synthetic strategy on a slide.

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15. CR on April 26, 2011 12:01 PM writes...

But how will we know that it is "exquisite" if K.C. doesn't tell us??

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16. Hap on April 26, 2011 12:17 PM writes...

#14: Funny, I thought that's what clear ChemDraw graphics (or, drawn ones, as per RBW) were for. How did people manage to get along without eye-scalding colors for so long, then?

Color is good if it makes something clear that couldn't be made clear in B+W. I'm not really seeing how color does that here. It also obscures the details of the rings, which seems counterproductive if clarity is the object.

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17. Frank on April 26, 2011 2:47 PM writes...

This may be one of the weakest articles I have seen appear in ACIE. Who cares about the colorful structures, what about the subpar chemistry? This is a synlett at best.

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18. Frank on April 26, 2011 2:48 PM writes...

This may be one of the weakest articles I have seen appear in ACIE. Who cares about the colorful structures, what about the subpar chemistry? This is a synlett at best.

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19. MoMo on April 26, 2011 3:06 PM writes...

KC is trying to liven up our boring, insipid lives as we stand in line at the soup kitchen.

Thanks KC, I am so happy now!

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20. Huskies on April 26, 2011 3:26 PM writes...

I have to agree with Frank, but the greater issue is the dilution of scientific literature. In the last year alone I have seen articles appear in Nature (DuBois or Johnston) that were not very important. This KC article is awful, my printer became sick from printing it.

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21. anonymous on April 26, 2011 3:50 PM writes...

These colored rings are extremely useful! They tell you that you are one click away from a useless and boring synthesis, which, needless to say brings nothing to the field.

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22. Hexanes on April 26, 2011 3:53 PM writes...

Actually, as bad as this publication is, it is peer reviewed and we have to support that process. Granted, this molecule as been around for 7 or 8 years and nothing substantial has been published. Even a quick google search of the molecule only reveals 1 dissertation from 2010 so any effort toward the synthesis is ACIE worthy.

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23. Anonymous on April 26, 2011 4:17 PM writes...

Say what you want, but at least KC cares enough about his people to publish their work. Some advisors will sit on results for years, at the expense of their kids.

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24. Anonymous on April 26, 2011 4:55 PM writes...

Talk about molecular editing...KC decided in his right mind to delete the C4 vinyl methyl, C8 methyl, C13 OAc, C12 quaternary center which comes from the missing lactone ring system, and finally the missing THF ring is this still a functionalized system ? Hexanes there are at least 5 groups working on this molecule, Lear, Sulikowski, Mulzer, Stoltz, KCN. I'm willing to bet there is more than 1 dissertation out there...hence it is not worthy of ACIE....the only reason why it was accepted was because of 1 thing. the name K.C Nicolaou, and no he didn't publish this for his students...he published it for himself because he thinks this may catapult him to a Nobel prize.

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25. Hexanes on April 26, 2011 5:10 PM writes...

Its obvious the chemistry probably wouldn't work in the presence of actual functionality! So I am sure this was KC's attempt to mark his turf, although the [2+2] has been demonstrated previously (in an OL and TL for that matter).

Although I agree with your point that this may not be ACIE worthy, I still think its important to protect the sanctity of the peer review process. Some editors believe its worthy and I have a hard time believing KC strong armed the review committee. He has over 700 articles, so one more isn't going to make or break him. For all we know Lear, Sulikowski and Mulzer gave him the green light for this paper.

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26. Anonymous on April 26, 2011 5:12 PM writes...

The colorful structures are meant to distract us from the landmines he calls a synthesis. At least its not a damn polyether again...sigh.

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27. Anonymous on April 26, 2011 5:28 PM writes...

With any molecule there are going to be good routes and bad routes. The bottom line here is that no matter how good or bad the KC route is, its published. If your work isn't published, it isn't discussed. So while many are working on this molecule, if they aren't putting it out for the masses, its irrelevant.

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28. anonymous on April 26, 2011 5:45 PM writes...

#27 ..."if they aren't putting it out for the masses, its irrelevant"...

It is also irrelevant to publish irrelevant stuff.

#24 Thinking that total synthesis will be awarded another Nobel Prize is insanity. Thinking that KCN will get a Nobel Prize for total synthesis is absolute insanity.

There is nothing wrong with KCN, what he does is fine but the glory days of total synthesis are way behind us. Chemists need to realize that.

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29. Anonymous on April 26, 2011 5:50 PM writes...

I'm seeing a lot of RED in those structures. Interestingly, it mirrors the "in the red" debt situation Greece...any connection here??

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30. Anonymous on April 26, 2011 5:54 PM writes...

If you believe in the "sanctity" of the peer review process, then it should be a double blind process with no mention of who's work it is. My issue is that if KCN's name weren't front and center would it have been accepted in ACIE? Therefore the science can speak for itself, and not a big name.

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31. Anonymous on April 26, 2011 6:15 PM writes...

Sulikowski, Lear...who are these people? Are they in the US or UK?

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32. Hexanes on April 26, 2011 6:20 PM writes...

I have absolutely no problem with a double blind process. Reviewers shouldn't know whose work their reviewing and writers shouldn't be able to request reviewers.

I can admit there is author bias (EJ and KC sometimes have incomplete supplementals) but I still believe reviewers wouldn't just give him a get out of jail free card (unless Snyer, Sorenson, and Baren were the reviewers).

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33. Chandra on April 26, 2011 6:29 PM writes...

Annoyingly colorful structures aside...this is bad chemistry. I've seen posters at ACS meetings on this target from Stoltz's and Sulikowski's lab and their chemistry is far superior. I would assume Trauner's biomimetic route is also novel.

I don't know the status of either project, but all both routes were far superior to this Angew. It takes a special type arrogance to suggest this is en route to the target. Shame on the editor's and the author.

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34. cascade on April 26, 2011 6:45 PM writes...

I am not the greatest fan of KC and his chemistry, however, this time I cannot stop appreciating his work. I have worked on this molecule for about two years with no significant progress and even the construction of a model system seemed difficult. KC's model is significantly more advanced than the earlier reports. I like the way they made the exo-enol ether from furan as that gave them the necessary breakthrough.

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35. Anonymous on April 26, 2011 6:47 PM writes...

What KC and many others want is a life time achievement award. They confuse that desire with the intent of the nobel prize, which is to award that which is groundbreaking. You simply cannot get the prize for figuring out 70 uses for IBX.

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36. Anonymous on April 26, 2011 6:49 PM writes...

Im writing my thesis...I should put all my structures in red and piss my boss off. He worked for KC, lets see him tell me they look stupid!

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37. Anonymous on April 26, 2011 6:53 PM writes...

Cascade, sure they formed the exo-enol ether, but they have absolutely no way to approach the target from this intermediate. It is devoid of functionality on the entire southern portion of the molecule. Like many others, I suspect a more functionalized molecule was unreactive. I don't know much about photochemistry, but I cannot imagine KC accepting this result as a starting point.

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38. Anonymous on April 26, 2011 7:01 PM writes...

This is hands down one of the most difficult structures published in quite a while. It is ridiculously functionalized and compact.

To my knowledge no other lab has demonstrated as much progress as the Nicolaou lab and if they have, do not blame him because those labs did not report their results.

Sure, its political and everyone doesn't have the power to push Angew. Chemie. BUT they do have the ability to publish in EJOC or OL. If they had, then Nicolaou's "inferior" results would have never made it to Angew. Chemie.

Bottom line, stop holding data. If you do and you get scooped then no one is to blame except the self.

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39. cascade on April 26, 2011 7:13 PM writes...

Anonymous: Thanks for the modesty about your knowledge of photochemistry. Building the precursor for the [2+2] is perhaps the biggest challenge in making this molecule (and thats why I said so about the exo-enol ether in my earlier comment). The ester function clearly has a very important role to play and that helps the [2+2]. It was actually very intelligent of the workers to put it there and not so intelligent of them to not mention/explain it. Making of such a complex framework was not precedented and now that it is it will help several other groups (including mine)to approach the target in that direction. If you are a graduate student, try not to get an impression of the chemistry from what others say....look into the details. I can clearly see how the actual molecule can be approached from this strategy....though there are still a few unknowns which nobody can really answer (making butenolide with a lactol around..or the vice-versa)

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40. Anonymous on April 26, 2011 7:23 PM writes...

Cascade: All in all i think it is a good paper, especially since there is such a void of information in the literature regarding efforts toward this molecule.

After the 2 early reports on this molecule, my group addressed this problem in group meeting and we knew the macrocyclization, the C12 Quat center and the C13 acetate would be serious issues. Nicolaou has addressed the macrocyclization nicely and I'm sure he has plans for the other two of these difficult issues.

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41. anonymous on April 26, 2011 7:49 PM writes...

Cascade + 38, 40
how is this ridiculously functionalized ? the whole thing is the definition of ridiculously functionalized.
the (2+2) was already established by Sulikowski (Vanderbilt) and Lear ( National University of Singapore) with photochemistry so what is new here? He made a macrocycle by lowering the bar so far...he could trip over it. Its hard to believe KC is seriously considering using what he has unless he wants to do like 4 C-H oxidations

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42. Anonymous on April 26, 2011 8:09 PM writes...

41. Nicolaou used the same key photochemical step as these groups did, except he generated key functonality on the the eastern region of the target.

Lets be honest, the Lear chemistry was nothing new. As far as the Sulikowski route is concerned, it's quite obvious his group was unable to add functionality to the core structure he synthesized in 2004. If they did, we would be reading about it as that would be an important advancement.

Odds are, he couldn't make that next key carbon-carbon bond to install the quat center and connect it to the carbon bearing the acetate group.

I worked for Trauner and I'm quite familiar with advancements to this family of molecules. I have heard nothing new from Vanderbilt or Singapore.

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43. FCC on April 26, 2011 8:23 PM writes...

The cascade in the synthesis is worth publication in Angew. Chem. Int. Ed. Some of the posters must not realize that Nicolaou is the single greatest chemical mind in the country, hands down.

His synthesis typically are more creative and efficient than any of his older peers like Danishefsky, Evans, Overman, and maybe even his mentor EJ. Think about it, his progeny are far more successful in academia and industry than anyone else's. Name a person who has placed more professors, other than EJ?

Someone who rejects his contribution is sick in the head.

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44. steve on April 26, 2011 8:37 PM writes...


We are all entitled to our opinions; but if thats really how you feel you should stop abusing opioids.

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45. Jose on April 26, 2011 8:48 PM writes...

"That Nicolaou is the single greatest chemical mind in the country, hands down." Not that, that is just rich!

Deletions, burning off FGs, redox stupidity, and a complete and total lack of elegance. Yes, that's just state of the art....

I always Zeus was all about bring flashy technicolor schemes....

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46. anonymous on April 26, 2011 8:50 PM writes...

42. Yes indeed it is an extremely difficult molecule to make, but you don't know if those groups are holding out for the whole thing. A truly worthy ACIE

43. This is exactly the kind of mentality that gets these types of papers published....the single greatest chemical mind blah blah.

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47. Jose on April 26, 2011 8:51 PM writes...

Wait, sorry, Lear is happily publishing current papers with
Xenobe Research Institute (XRI) and JJ La Clair as a co-author?


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48. JJ on April 26, 2011 9:07 PM writes...

I have been a KC basher most of my adult life. His syntheses are long, boring and non-educative. My impression about that group, and my expectations from that group to do some ‘killer’ chemistry were never too high and I believe that he does everything for getting there first. This time it’s different (hate to say that!).
The paper has all the qualities that I did not expect from KC. Its short, it has a couple of interesting transformations (out of five!), and it lays a solid foundation for further exploration. I agree with ‘cascade’ that the sequence has chemistry and strategy which, perhaps, only a thinking chemist can interpret and appreciate. Looks simple….but has more to it. It’s more like EJ-type rational thinking coupled with Danishefsky-type implementation and I give KC full credit for coming up with such a route to test the hypothetical biosynthetic route. Just as much as I think that this is so not the usual KC-type synthesis, I think that he has not done justice writing it up, again unlike KC (he usually makes ordinary work sound good….this time he has got it the other way). Honestly, is this really KC!

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49. Rasheed on April 26, 2011 9:19 PM writes...

I think the chemistry is well executed and concise...but I think the presentation of the material was lacking and uneducational...odd, seeing that KC went through an entire ordeal recently discussing education.

In the isolation paper the authors proposed this type of photocycloaddition to form the cyclobutane. This however, is not realistic...I don't think photochemistry occurs at the depths of the ocean and typically cyclobutanes are synthesized in nature through cationic cyclizations. Although it looks cool, I doubt this is how nature makes this ring system.

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50. Being the peanut gallery on April 27, 2011 12:05 AM writes...

Apropos of nothing, I'm just chortling over the fact that someone has initials spelling "potassium cyanide."

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51. Spiny Norman on April 27, 2011 12:06 AM writes...


ex·quis·ite/ekˈskwizit/ Noun: A person who is affectedly concerned with appearance.

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52. ANON 2 on April 27, 2011 6:05 AM writes...

I think comment 51 sums it up, yet I'll add. I have forever disliked the distracting nature of his graphics. Black and white chemdraw overheads tell the story just fine...worked fine for his Ph.D advisor.

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53. Young Padawan on April 27, 2011 6:19 AM writes...

Excerpt from the urban dictionary:

1) To use a very large excess of a reagent. To bomb it. 2) To fill all one's cyclic structures with colors.

10 equivalents

"Hey how much MnO2 should I use?"
"2 or 3 Nicolaous should do it."

"Hey what's with that structure? It's full of strange colors!"
"Oh, I Nicolaoued it."

"Nothing's happening with my reaction..."
"You should just Nicolaou it."

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54. Anonymous on April 27, 2011 6:56 AM writes...

49/ I have to agree with you. Some consider the [2+2] as the "obvious" disconnect, but this tool isn't really in natures toolbox. It is without question a cationic process, which is what the authors of the isolation paper elude to.
Its like the phantom and mysterious "diels alderase". As chemist, we see a disconnect and want so bad for it to be in line with nature.

Now, to be in line with the topic of the thread, the graphics blow, but they serve their purpose, we're talking about them.

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55. anon on April 27, 2011 7:07 AM writes...

All the chemistry comments aside (and I agree), the first thing I thought of when I saw this post was the Greek God and Goddesses KCN used to put on his slides. The first time I saw him talk as a grad student I literally could not stop laughing. I kept thinking "when is he going to be done with these 'intro' slides and show some normal structures?" You all know that it never stopped. I was amazed, and disgusted.

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56. Anon on April 27, 2011 7:11 AM writes...

"By Hera's headress! Kyriacos, m'boy, I've been perusing this 'JACS' all the Americans go on about, and I've noticed there simply aren't enough urns, frescos, and murals to liven up the pages. How could this Stork publish this article without a picture of the Acropolis?

KC, we're sending you out into the wider world to bring that flavor to modern chemical publishing. Good luck, and here's your paint set and colored pencils. You leave tomorrow"

-Cyprus, 1964

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57. Anonymous on April 27, 2011 7:56 AM writes...

^^ I also saw KC give a lecture at Columbia, in which he discussed polyethers for 50% of the talk, with idiot graphics. For the other half, he discussed the history of Columbia Chemistry. I have no clue how much they paid him to give that talk, but it was ridiculous. The slides are actually on his website.

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58. cascade on April 27, 2011 8:25 AM writes...

41: FYI Lear uses allene (a more or less ideal substrate for a [2+2]) and Sullikowski uses a lactone (I am actually a bit hesitant to call Lear's model as a model for bielshowskysin). KC has the hemiacetal in the right place....and I think that similarity as close as it may appear (to you), makes a huge difference. It adds a lot of importance to the paper (search for such systems with ketone on one side and hemiacetal on the other) and count the number of hits. I think its completely "odd" to compare KC's route with Lear and Sullikowski. About functionalization, in our group meeting today we had an exercise as to how this strategy can be used to make the real deal....and we came up with plenty of resonalble schemes (and got the boss thinking of re-starting this project)!! And about KC publishing this result....I wish others do the same as they have been holding on to it for too long....really... 7 years! The only complain I have about this paper is that not much is revealed as far as chemistry goes and that is bad, political and scientifically discouraging.

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59. Anonymous on April 27, 2011 10:30 AM writes...

Cascade, I have great appreciation for this paper because of how concise the route is, but I actually have to disagree with you about the magnitude of the contribution. I agree that demonstrating the photochemistry in the presence of the acetal is critical, but the molecule has several features that are far more difficult to install, none of which are present in this paper. As mentioned earlier, the C12 quat center, the chiral center at C13 and the stereochemistry of the lactol featuring an exo-methylene group are more pressing issues.

I think this paper belongs in EJOC. Following the advice of Comment 22, a proquest search revealed 2 thesis on this molecule. Those groups could have easily attempted to publish, but they held back. Lets call this what it is, an elegant data dump.

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60. Anonymous on April 27, 2011 10:48 AM writes...

Everyone is harping on KC for publishing on this molecule, when in reality the anger should be aimed at groups that hoard data. Leer likely has nothing. Trauner probably trashed the project to focus on neuroscience. Sulikowski hasn't published in 7 years, which is a red flag as far progress is concerned. His initial paper featured a synthesis that really backed them into a corner. I'd imagine his lab was unable to achieve photocycloaddition of a substituted butenolide which means their efforts ran into a dead end. My boss personally thinks he has trashed the project years ago. Speaking in the present, the only progress we have really, is KC's. This is now the standard for publishing on this molecule. As far as graphics are concerned, they aren't that bad. every author has their own style. If its not against editing rules, who cares.

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61. GPK on April 27, 2011 10:57 AM writes...

I worked on this target with Kathy Parker and I think bashing other labs is way out of place. Everyone doesnt have KC's army to push molecules. Other groups may have 1 or 2 people working and in this case it takes them a very long time. People are overemphasizing the importance of this contribution. KC has been working on this since '04. If this is the best he has, he should retire.

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62. RM on April 27, 2011 2:04 PM writes...

Only KCN can publish synthetic progress on a natural product and put it in Angewandte. He will not finish the target with this method. It´s just another dead end. Sad but true, the editor from Angewandte adores him, so do the reviewers. In fact, I don´t know any colleague who wrote a negative review against one of Nicolaou´s papers.

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63. MrButenolide on April 27, 2011 5:00 PM writes...

@anonymous (#60): Trauner has not trashed the project to focus on neuroscience. He does both awesome total synthesis and neuroscience..

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64. jj on April 27, 2011 10:57 PM writes...

62: Read some recent papers from Angew and you will find some ridiculous formal syntheses, some incomplete studies and some real plain crap total synthesis of infinitesimally small and not so complex structures. More importantly, and much against the popular beleif, these papers are from not-so-well-known groups and not-so scientifically established countries!!! We just love bashing KC as we expect him and his students/postdocs to comeup with a flawless synthesis. I personally liked the paper and dont see anything wrong with that being published here. I also ridicule the idea that other groups are holding there guns for the total synthesis. For molecules like taxol, plauamine, vinigrol several "studies towards" papers came out before somebody actually made them. KC has started the race on this one. I am a medicinal chemist and loved the way KC made these structures.

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65. Hap on May 23, 2011 9:39 AM writes...

62: Alas, no. See, as a counterexample, Porco's synthesis of part of the kibdelone core (ACIEE, 2011, p. 2511).

It's still kind of lame, but KCN isn't the only one doing it.

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66. Hap on May 23, 2011 9:41 AM writes...

62: Alas, no. See, as a counterexample, Porco's synthesis of part of the kibdelone core (ACIEE, 2011, p. 2511).

It's still kind of lame, but KCN isn't the only one doing it.

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67. A1 on August 2, 2012 9:08 AM writes...

Hi All,

I am thinking to post a picture to "birthday present to KCN" contest. Can some body educate me as to how to color the inside of the rings? What program does he use? Looks like it is not that trivial an art!

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