~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).