The Realm of Organic Synthesis

We had an awful time at the Olive Garden the other night, which prompted me to fire off an email to their corporate offices complaining about the level of service.  The squeaky wheel gets the oil; they thanked us for our comments and are sending a gift card in the mail as an apology.  Not a bad way to start off a Friday morning.

It’s all about lithium enolates today.  It’s been quite some time since I last used any lithium reagent (properly), so I decided to brush up on the basics as a refresher.  The University of Rochester has an impressive website entitled “Not Voodoo,” which features the rudimentary concepts of synthetic organic chemistry along with a few pearls of wisdom intertwined (http://chem.chem.rochester.edu/~nvd/).  There’s a very interesting laboratory guide that’s perfect for the inexperienced organic chemist, Advanced Practical Organic Chemistry by Leonard, Lygo and Proctor (ISBN: 0 7487 4071 6).  The book covers all of the basics without going into excruciating detail and/or half-directions—characteristics of many Ph.D.’s. 

While on the subject of standard operating procedures, as many of you know, Perrin and Armarego published an excellent book entitled Purification of Laboratory Chemicals (ISBN 0 7506 3761 7), which has recently been a personal favorite.  It’s pretty much an encyclopedia preparing a number of reagents for reaction-level purity (organic and inorganic).  The best part is that the majority of the purification procedures have references for primary literature (if that sort of thing matters to you). 

Switching gears, what’s up with the Red Sox as of late?  We once had a 12-game lead on the Yanks, and now we’re down to 7 1/2 after losing a 3-game series to the ROCKIES at Fenway.  Maybe we can get the bats swinging against San Fran this weekend.

On a more personal level, there’s a great article in the Crimson White about how UA is extorting engineering students out of their football tickets this upcoming semester: (http://media.www.cw.ua.edu/media/storage/paper959/news/2007/06/14/Opinion/CoOp-Students.Unfairly.Denied.Tickets-2915148.shtml?reffeature=mostemailedtab).  That author must be a genious.

Have a great weekend.

I spent the better part of the morning looking for the cat, for fear that she had wandered outside.  After searching for nearly an hour, I finally called Kerri to let her know the news; Miss Piggy was gone!  When Kerri got home, she literally tore the house apart looking for the awfully vocal tabby cat.  It turns out that the feline in question was hiding in the recliner (literally, up inside the wood-metal frame).  As loving parents, we grounded Miss Piggy for a week and took away the catnip (..kids today).

So, now the shock has worn off, and now I’m back at the lab ready to get some work done.  I wonder, though, why no one has come up with a simple method for converting primary alcohols to their corresponding iodides without making triphenylphosphine oxide as a byproduct—a pain in the neck to remove and possibly the most atom uneconomical transformation known to the synthetic world.  Typical procedures involve treatment of the alcohol with PPh3, I2 and a fair amount of imidiazole to “kick it up a notch.”  Olah and co-workers wrote a review about the utility of pyridinium poly(hydrogen fluoride) in the presence of NaI (JOC 1979, 44, 3872), but the chemistry seems to only work for electron-donating or electron-stagnant reactants in fair yields.  An iodination that cleanly affords the desired primary halide without easy to remove byproducts with a fair degree of atom economy would make a fantastic original research proposal idea. 

Off to play with phthalic anhydride (seems to be the reagent of the day—http://orglist.net Everybody Digest, Vol. 35, Issue 10), so I can get home and watch the season premier of Rescue Me on FX.

Welcome to the Realm of Organic Synthesis.  I recently read an article about personal success and self-marketing.  One of the several keys in the article (apart from constant networking, developing an identity, etc.) was to start writing about something you know.  For me, what better way than by writing about my experiences in the lab and overall research? 

So, how about a little background?  I’m currently a graduate student at the University of Alabama in Tuscaloosa.  I work for (or “with”) Dr. Tim Snowden on developing new methodology for applications to natural product synthesis.  To the layman, we’re coming up with new, groundbreaking ways to make very complex molecules that exhibit a variety of therapeutic value.  Often these molecules are cytotoxic, particularly to cancerous cells.  So, in an oversimplified explanation, we’re trying to cure cancer.

The general aim of this weblog is to introduce you, my audience, to the field of synthetic organic chemistry through my lab experiences, interesting articles I’ve recently come across about science (chemistry in particular) and the occasional thought (my extensive liberal arts background has made me a proponent of philosophy). 

Welcome to the blog, and I hope you gain a little insight into the vast ocean of organic synthesis.