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The Impact of Nobel Prize in Chemistry on Fine Chemicals

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The Impact of Nobel Prize in Chemistry on Fine Chemicals MILESTONESFROM THE SCIENTIFIC IN CHEMISTRY ADVISORY BOARD Ian C. Lennon The impact of Nobel Prize in Chemistry on fine chemicals IAN C. LENNON Member of Chimica Oggi/Chemistry Today’s Scientific advisory board s this is the “2011: International Year of Chemistry” it is opportune to reflect on the impact that the Nobel Prize in Chemistry has had on the pharmaceuti- Acal and contract manufacturing industries. Between 1901 and 2010 the Nobel Prize in Chemistry has been awarded 102 times to 160 Nobel Laureates for achieve- ments in a diverse range of chemistry, from polymers to biological chemistry, struc- tural and surface Chemistry, to quantum mechanics. This editorial will focus on those Nobel Prizes that have had the biggest impact in the manufacture of pharmaceuti- cals and fine chemicals. By the start of the 20th Century chemical manufacturing was well establi- shed in Europe and many new reactions and techniques were being developed. The 1902 No- bel Prize in Chemistry awarded to Emil Fischer for his work on purine and sugar synthesis was hi- ghly significant. Fischer has >8 reactions named after him, including the Fischer Indole synthesis and the Fischer reduction. The 1912 prize was shared between Victor Grignard and Paul Sabatier. 2 We can all appreciate the impact of the Grignard reaction to enable the synthesis of alcohols and for- ming new carbon-carbon bonds, but Sabatier’s work on developing methods of hydrogenating organic compounds in the presence of finely disintegrated metals, was an equally important milestone in organic chemistry. A few industrial chemists would dispute the fundamental importance of Fritz Haber’s work on the synthesis of ammonia, which led to the 1918 prize, though awarded in 1919 as no candidate met the criteria to receive the award in 1918, so it was deferred for one year. Haber’s work led to the manufacture of fertili- zers and explosives, very important during the First World War. He was also known as the “Father of chemical warfare”, not an accolade we would all like to share. Can you imagine making complex natural products or stereochemically congested rings without the Diels- Alder reaction? Otto Paul Hermann Diels and Kurt Alder received their Nobel Prize in Chemistry in 1950, followed by Linus Pauling in 1954 for his work on the nature of the chemical bond and its application to the elucidation of the structure of complex substances. In the golden era for natural product synthesis that was to follow new methods for constructing carbon-carbon bonds and elucidating complex structures transformed chemistry from a science to an art. Arguably, the preeminent organic chemist of the twentieth century Robert B. Woodward received his prize in 1965 for outstanding achievements in the art of organic synthesis. Woodward made key contributions to the synthesis and structure determination of complex natural products. Major advances in organometallic chemistry were pioneered by Ernst Otto Fischer and Geoffrey Wilkinson and they shared the Nobel Prize for Chemistry in 1973. Wilkinson was well known for the discovery of the structure of ferrocene and the invention of Wilkinson’s catalyst, which led to the development of homogeneous catalysts for many reactions, including asymmetric hydrogenation. The most successful and widely used pharmaceuticals of the last 20 years have been single enantiomers, such as Lipitor, Plavix and Nexium with combined sales of over $30 Billion in 2009. Therefore it is important to acknowledge the contributions of Vladimir Prelog for his research into the stereochemistry of organic molecules and reactions. Of course we all know the Cahn-Ingold-Prelog priority rules. Prelog shared the 1975 prize with John Cornforth, who worked on the stereochemistry of enzyme-catalyzed reactions. In the area of peptide chemistry many new drugs could not have been developed without the contributions of Robert Bruce Merrifield, who invented solid phase peptide synthesis and the famous Merrifield resin. He received his prize in 1984. In recognizing the impact of fundamental reactions to form new carbon-carbon bonds and extend the scope of organic synthesis, the Nobel committee gave the 1979 award to Herbert C. Brown and Georg Wittig for their work developing new boron reagents and phosphorous containing compounds, respectively. chimica oggi/Chemistry Today - vol. 29 n. 3 May/June 2011 FROM THE SCIENTIFIC ADVISORY BOARD The Wittig reaction is one of the most important and widely applied methods to synthesize double bonds. Over the last twenty years there have been many significant Nobel Prizes in Chemistry that have impacted organic synthesis. In 1990 the prize was awarded to E. J. Corey, known best for his work on prostaglandin synthesis and the CBS reduction. Many of us have a copy of his inspirational tome “The Logic of Chemical Synthesis”. The importance of metal catalyzed homogenous catalysis is highlighted in the following three Nobel Prizes for Chemistry. In 2001 William Knowles, Ryoji Noyori and Barry Sharpless shared the prize, Knowles for his pioneering work in asymmetric hydrogenation, developing the first industrial scale process for L-DOPA; Noyori for the development of the Binap family of catalysts; and Sharpless for developing asymmetric epoxidation and dihydroxylation reactions. These methods are now used routinely in pharmaceutical manufacture. Another methodology now widely used for chemical manufacture, is metathesis which was recognized in 2005 when the prize went to Yves Chauvin, Robert H. Grubbs and Richard R. Schrock. Finally, the long overdue Nobel Prize in Chemistry, for the most important of carbon-carbon and carbon-hetero atom forming reactions, palladium catalyzed cross couplings, was awarded jointly to Richard F. Heck, Ei- ichi Negishi and Akira Suzuki in 2010. Who has not heard of the Heck reaction, the Negishi coupling and the Suzuki coupling? “Standing on the shoulders of giants” is a phrase made famous by Sir Isaac Newton. It is clear to see how each of the discoveries and advances that has led to Nobel Prizes in Chemistry, has relied upon the pri- or understanding and achievements of earlier chemists, going back many decades. The technologies hi- ghlighted here will provide the platform for new generations of chemists to continue expanding the scope 3 of organic synthesis. chimica oggi/Chemistry Today - vol. 29 n. 3 May/June 2011.
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