Saturday, September 5, 2009

Poor Pigs

A new strain of swine flu influenza a H1N1 virus is spreading around the globe. The WHO declared 2009 swine flu pandemic - First Phase 6 Influenza pendemic Since 1968.



(_)-Oseltamivir phosphate (Tamiflu), a neuraminidase inhibitor used in the treatment of both type A and type B human influenza,Currently the most effective drug for the treatment of Influenza. But the unmet supply of this drug demand urgent solutions. The manufacture of Tamiflu by Roche Company utilizing naturally occurring shikimic acid as the starting material. Getting stable quality of pure shikimic acid may be problematic.

The Tamiflu supply problem has piqued the attention of academic chemists. It is known that several labs have already reported new methods in making Tamiflu without shikimic acid. But it is very difficult to evaluate academic syntheses from the standpoint of potential as a manufacturing process because they have not been developed for the large-scale operation. Considering the amount of Tamiflu required worldwide, there is an urgent demand to improve the production process.



Here is the retro synthetic analyse for the short cut synthesis of Tamiflu.
This syntheis intiated by oxa-Michael addition of alcohol to acrolin, which was reported by Zhang et al,

3 comments:

LCMS said...

Good post. Nice, elegant and economical synthesis of intermediate that could lead to Tamiflu. Authors have been careful not to mention Tamuflu in the paper. Kudos to you for spotting the "hidden" application!

Sabin said...

The azide nitroalkene you suggested possibly reacts in a cycloaddition to give nitrotriazole. Does this reagent exist? Nice idea anyway.

Medicinal chemist said...

nice information! and quite useful for present situation.