Prospecting for alternate sources of shikimic acid, a precursor of Tamiflu, a bird-flu drug

• Main Authors: Raghavendra, TR, Vaidyanathan, Priti, Swathi, HK, Ramesha, BT, Ravikanth, G, Ganeshaiah, KN, Srikrishna, A, Shaanker, R Uma
• Format: Article in Journal/Newspaper
• Language: unknown
• Published: Indian Academy of Sciences. 2009
• Subjects: Organic Chemistry; Ketal; Avian flu
• Online Access: http://eprints.iisc.ernet.in/26104/; http://eprints.iisc.ernet.in/26104/1/771.pdf; http://www.ias.ac.in/currsci/mar252009/contents.htm

Shikimic acid, more commonly known by its anionic form, shikimate, is an important intermediate compound of the ‘shikimate pathway’ in plants and microorganisms1. It is the principal precursor for the synthesis of aromatic amino acids, phenylalanine, tryptophan and tyrosine and other compounds such as alkaloids, phenolics and phenyl propanoids2. It is used extensively as a chiral building block for the synthesis of a number of compounds in both pharmaceutical and cosmetic industries3. In the recent past, the focus on shikimic acid has increased since it is the key precursor for the synthesis of Tamiflu, the only drug against avian flu caused by the H5N1 virus4,5. Shikimic acid is converted to a diethyl ketal intermediate, which is then reduced in two steps to an epoxide that is finally transformed to Tamiflu6.