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Chem 30CL- Lecture 1c

Chem 30CL- Lecture 1c - Lecture 1c Click to edit Master...

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Click to edit Master subtitle style 8/6/11 Asymmetric synthesis Lecture 1c
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8/6/11 Hanson, J., J.Chem.Educ. 2001 , 78(9) , 1266 (including supplemental material ). Larrow, J.F., Jacobsen, E.N., Org. Synth. 1998 , 75 , 1. Cepanec, I. et al., Synth. Commun . 2001 , 31(19) , 2913. Flessner, T., Doye, S., J.Prakt.Chem. 1999 , 341 , 436. McGarrigle, E.M., Gilheany, D.G., Chem.Rev. 2005 , 105(5) , 1563. Schurig, V., Nowotny, H.P., Angew.Chem. Int. Ed. Engl . 1990 , 29(9) , 939. Assigned reading
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8/6/11 Chirality plays important key role in many biological systems Many drugs are single enantiomer drugs because often only one enantiomer is active in a desirable fashion while the other enantiomer is harmful Some of these drugs are isomerized in vivo (*) Why asymmetric synthesis? Drug R-form S-form Thalidomide Morning sickness Teratogenic* Ibuprofen Slow acting Fast acting* Prozac Anti- depressant Helps against migraine N O O * NH O O COOH
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8/6/11 History of Asymmetric Synthesis I 1848 Louis Pasteur discovers chirality 1912 Bredig and Fiske conduct first
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