Sick Again? Oh Dear! Get Oseltamivir!

~If you’re like so many who are sick with the flu, then perhaps some Oseltamivir is for you!~

Oseltamivir, or more commonly known as Tamiflu®, is a commonly prescribed antiviral drug used mostly in the prevention and treatment of certain cases of influenza.¹ Though Oseltamivir’s trade name is Tamiflu®, its IUPAC formal name is:

ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate. ²

Though there are several methods to synthesize Oseltamivir, the reaction scheme shown below highlights the implementation of a Diels-Alder, or pericyclic, reaction in the first step.³ (Emphasis on the Diels-Alder reaction with the yellow highlight box was added by the blog author).

...and now you know. Next time you have the flu, you may just have to take time and pay your respects to the Diels-Alder Reaction.

References:

1) Mayo Clinic. Oseltamivir (Oral Route) <http://www.mayoclinic.com/health/drug-information/DR601671> (Accessed Feb 11, 2013).

2) ACD ChemSketch, version 2009; Advanced Chemistry Development, Inc.; (Accessed Feb 11, 2013).

3) SynArchive.com: The Organic Synthesis Archive. Oseltamivir. <http://www.synarchive.com/syn/149> (Accessed Feb 11, 2013).