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Synthesis of the Year, 2006   

18 January 2007 4,149 views 14 Comments

Yup, the title says it all. I had planned to do this for a while, but I was forgot in the hiatus of The Move. However, a more thorough investigation of the brilliant ChemBark led me to a reminder! I’m leaving it up to you lovely readers to suggest your favourites, then I’ll add a poll of ten (in a week). Once a synthesis has been suggested, it’s been suggested, so there’s no need to post it twice, and please add a DOI if I didn’t blog it (shame on me!).

Slainte Mhor, Paul.

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  • ddd says:

    Since some synthetic chemist switched from natural product synthesis to natural product isolation, I propose an “isolation” of the year….Wender’s Isolation of the Apoptolidins…

  • Mbombok says:

    also, Boger’s synthesis to vindoline was pretty cool…

  • What’s the score with the explosion?

  • JamesB says:

    Yes, please enlighten us as to this local news making bang.

  • Mike says:

    For those who don’t know what TM and JB are talking about – this explosion.

  • .... says:

    Was there any Science/Nature total syn in 2006?

  • Tot. Syn. says:

    Umm, I’m not commenting on the explosion, because all I know is in that BBC article. I guess I’ll find out more later, but the fire brigade were very praise worthy of the lab worker’s response. Everything is business as usual here now.

  • WillisWill says:

    Good job by the students to put the fire out, hopefully the glass injuries aren’t too severe.

    Explosion stories are always enlightening. Often we can learn better lab practice from them. I’ll share my own.

    When I was a grad student, it was practice in my group to carry out recryst’s by using a heat gun (ie hair dryer) to heat the solvent. One time I was doing a recrys (in the hood of course) from hexane. I realized I needed more solvent in the flask. I turned the heat gun off and set it on the side of the hood. I pulled up a pretty full 4 liter bottle. As I tried to pour the hexane directly into the flask, I think some of the vapor made its way to the heat gun, which promptly ignited on the still hot electrical coils. The flame quickly jumped back to the bottle itself, leaving me standing with what appeared to be a 4 liter Molatov cocktail! There were plenty of intelligent things I could have done at this point (like through the bottle into the hood and close the sash), but only rarely do I do the intelligent thing (usually it’s by mistake when I do) So instead I dropped the bottle onto the floor, where it quickly broke and spread now flaming hexane throughout the lab area. It made its way to our stack of paper towels in the corner, and promptly set them on fire as well. The sprinklers came on and put the fire out (a mess in itself) Thankfully no one was hurt and no expensive equipment was damaged.

    Moral of the story – heat guns are convienant, but dangerous. If something’s on fire, try put it in the hood.


  • Russ says:

    I did a postdoc in a lab where an emerging reaction was being developed that ran under an atmosphere of oxygen (at reflux). Without giving too much thought to it, the student on the project tried the reaction in THF, and it exploded impressively. It quickly became policy thereafter that reactions under O2 would not be done in flammable solvents (which in retrospect, is a pretty logical policy…)

  • milkshake says:

    I am currently running a bunch of experiments under O2 baloon in toluene at 80C – and it did occur to me that a spark would produce a strange experience….Like Apollo 1.
    I guess some perhalogenated solvent would be a good idea; unfortunately this cyclization reaction is very finnicky about the solvent and those replacement solvents that I tried did not quite work.

  • ddd says:

    How do you usually work up your reaction mix after reductive amination with NaBH3CN? I have acid labile substrate so I cannot use HCl. I think work up with pH>7 would work also?

  • milkshake says:

    10% NaOH should do. Also Raney Ni catalyses decomposition of amine-borane complexes in neutral pH but it takes some time.

  • Johan says:

    I think the Synthesis of Chartellin C by Baran was brilliant – wasn’t it synthesis of the month?

  • Zinc says:

    I nominate the 11-O-debenzoyltashironin by Danishefsky.