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Tamiflu – put that flask down; back away from the fume hood!   

12 January 2009 6,654 views 5 Comments

Just a quick news-nugget before I get on with the real business of the day – phorbasin C – but even though the Hayashi synthesis of Tamiflu is super-sweet, it may be a waste of time.  There’s a slightly worrying article about it’s uselessness against the most prevalent USian strain of flu over at the NWTimes. The article goes on to suggest that GSK’s Relenza might be a better bet for now.  Now, any smart ideas? I can see a SAD, potentially a Knovenagel, and maybe an Evans Aldol…

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  • Russ says:

    I’d be tempted to start out with glucose, which I think would set all the stereocenters from the tail, into the acetamide. From there, I’m guessing one could come up with substrate-stereocontrolled steps…

  • SiO2lungs says:

    To me it’ll be fun to try a [1.2] Wittig of a glycoside (from the corresponding dihydropyranose) so as to form the secondary alcohol closest to the ring. Yields of these rearrangements are not great but the stereoselectivity can be high (check Nakai’s work : J. Am. Chem. Soc. 1996, 118, 3317-3318 )

  • Liquidcarbon says:

    Before you grab that new flask though read about the huge bioavailability problems of Relenza.

  • Dennis says:

    Although the NYtimes article mentions potential resistance transfer, I think Tamiflu resistance in any new pandemic strains would be minimal. Therefore new syntheses and cheap routes to the drug may yet be valuable.

  • Stuart says:

    As a GSK shareholder, I find this news reassuring. Goes to show, the worst thing you can do for an antiviral is use it!

    Of course it’ll be all change next year. Flu is like that.