Organic Synthesis

I'm sure many of you will know who I am... so leave you all to guess if you don't know.

I'm posting because poor Mr Koh is the lonely one posting only to dunno-who's-reading. So allow me to contribute my fair share of knowledge on Science ===> Chemistry.

You get headache... what do you eat? Panadol? Do you know what's in your panadol that makes it work? (If you don't know start reading the contents of every drug you come across.) Well, it's called paracetamol (allright I've told you). But do you know how it works? And more importantly (to me), do you know how to synthesize it?

Organic synthesis was, and is, a very important field in science today. Back in the past, the importance was to be able to synthesize alkaloids e.g. quinine (for anti-malaria) so that we need not be overly reliant on the raw materials from trees, but could instead use simpler raw materials that are readily available, and can thus produce the alkaloid in larger quantities.

So what's the significance today? Simple. You know bird flu? Avian Influenze H5N1? (For your information, H stands for Hemagglutinin subtype 5 and Neuraminidase subtype 1 (out of 14 and 9 respectively). They are cell-surface glycoproteins. (Don't know? Go read up!)) What's the drug that Roche produced to treat Avian flu? Oseltamivir (a.k.a. Tamiflu). How does it work? I don't know. But more importantly, if it works, then get more of it! But how on earth do you get more of it when it comes from star anise, and you can buy up all the star anise in the world yet it's still not enough to produce enough pills for everyone in America and Europe? The answer lies in retrosynthesis and organic synthesis. Using strategies to make bonds etc. and using all available organic reactions known till date, you get now not 1 or 2, but 3 different ways to make Tamiflu. Wanna see the reaction scheme?

Oseltamivir

Ok so tell me what you feel. *What the... what is this?* or *Lost...* or *Oh my god this is SO cool!!!* (yea right... -.-")? I do believe many of you will feel overwhelmed by this huge reaction scheme, when most of you barely learnt much organic chemistry in sec3/4. This is a teaser to show you the peak of organic chemistry, the application to serve mankind most directly. But of course to be able to do all this you need to first digest many Chemistry textbooks and notes with Muggase (Note that muggase is produced by your brain, and not your stomach.) and pass all your chemistry tests and exams.

Hard work isn't it all? But I dare tell you that half of you will find organic chemistry the easiest out of all the chemistry components in A-level Chemistry (*looks left... looks right... Ok Mr Sam Lee not here... continue!) What you will learn this 2 years will barely scratch the reactions shown above. But then again, it's a teaser for you all.

The point in showing all these is that organic chemistry is 1. fun, 2. visual (compared to crunching equations for physical chemistry (Mr Teo dun come after me pls...)) 3. important in terms of applications. If you look up the Nobel Chemistry prizes, you will learn that so many of the awardees received it because of organic chemistry (and biology fields. amazing? protein structure!) To date organic chemists have synthesized countless alkaloids, all for the hope of making drugs and stuff so that man will live a better and longer life with lessened pain. Lemeshow you how difficult organic synthesis can be. Many of you should know Vancomycin, the last line of defence against bacterial diseases. This is the structure of Vancomycin:

Vancomycin

Complicated right... this is the kind of complexity that many of us have to grapple with to find pathways to synthesize. But if we don't tackle such challenges, then we'd have one less drug to treat diseases and infections. Vancomycin is a very important drug, as is Tamiflu.

I'm putting all these partly because I like organic chemistry and total synthesis. Organic chemistry is really the easiest to score in chemistry here, and is the most visual side of theoretical chemistry compared to... Schrodinger equation... (we also tackle quantum chemistry... it's no fun =( sad...) I'm also putting all these to stimulate your interest in Chemistry and Organic chemistry, and of course... to encourage you all to join Chemistry olympiad (So now you think you know who I am?). Chemistry can be fun and enjoyable once you get past the dry bits of basics. Inorganic chemistry there's all the colourful complexes that you can make with transition metals etc (the colours are really nice, especially once you crystallize them), and organic chemistry there's all the drawing that you do. Math and physics-inclined people will like physical chemistry. But it's all down to one thing: to serve mankind.

Suggestion to Mr Koh here: perhaps you could organise a trip to GlaxoSmithKline to see their pharmaceutical industry in Singapore, and what really goes on in a pharmaceutical industry. The trip that I went really stimulated my interest in Chemistry.

Chemistry isn't just *n is for the quantum level of your orbitals... there are s,p,d,f orbitals ... ... ... * sian right? Here's something to make chemistry more interesting through jokes and laming:

The romantic Diels-Alder reaction: the diene and the diene-lover.

If you all don't get that... please go Wiki and look up. All images from above are from Wikipedia.

Also, I've included links to papers and articles that you all might want to read up on.

The Art and Science of Total Synthesis (79 pages)

The Essence of Total Synthesis (On the right click Full Text (pfd)) (9 pages)

Molecules of the Month - Oxford (Colourful)

Molecules of the Month - Bristol (This one is more interesting)

Allright, hope you all enjoy! Happy cny!

Regards,
Hadriel Eeyore

Edit: Arrgh! how to show the full thing? Looks terrible! But anyway, if you want to see the whole thing go Wiki "Oseltamivir total synthesis"