Things have been getting more and more complicated here in CrashCourseOrganicChemistry, and as we deal with more complex molecules, parts of molecules we don’t want to react will start reacting along with the parts that we do. Luckily, we have protectinggroups, which act like a chemical disguise and help control how molecules react. In this episode, we’ll look at what makes a good protecting group, as well as identify some good protectinggroups for different functional groups. We’ll also see what role protectinggroups play in the synthesis of penicillin!
Series Penicillin References: Nicolaou, K. C., & Sorensen, E. J. (1996). Classics in total synthesis: targets, strategies, methods. John Wiley & Sons. Sheehan, J. C. (1982). The enchanted ring: the untold story of penicillin. Primary literature for Sheehan’s penicillin synthesis: Sheehan, J.C. & Izzo, P.T. J. Am. Chem. Soc. 1948, 70, 1985: Sheehan, J.C. & Izzo, P.T. J. Am. Chem. Soc. 1949, 71, 4059: Sheehan, J.C. & Bose A.K. J. Am. Chem. Soc. 1950, 72, 5158: Sheehan, J.C., Buhle, E.L, Corey E.J., Laubach, G.D. & Ryan J.J. J. Am. Chem. Soc. 1950, 72, 3828: Sheehan, J.C. & Laubach, G.D. J. Am. Chem. Soc. 1951, 73, 4376: Sheehan, J.C. & Hoff, D.R. J. Am. Chem. Soc. 1957, 79, 237: Sheehan, J.C. & Corey E.J. J. Am. Chem. Soc. 1951, 73, 4756
Series Sources: Brown, W. H., Iverson, B. L., Ansyln, E. V., Foote, C., Organic Chemistry: 8th ed.: Cengage Learning, Boston, 2018. Bruice, P. Y., OrganicChemistry, 7th ed.: Pearson Education, Inc., United States, 2014. Clayden, J., Greeves, N., Warren., S., OrganicChemistry, 2nd ed.: Oxford University Press, New York, 2012. Jones Jr., M.: Fleming, S. A., OrganicChemistry, 5th ed.: W. W. Norton & Company, New York, 2014. Klein., D., Organic Chemistry: 1st ed.: John Wiley & Sons, United States, 2012. Louden M., Organic Chemistry: 5th ed.: Roberts and Company Publishers, Colorado, 2009. McMurry, J., OrganicChemistry, 9th ed.: Cengage Learning, Boston, 2016. Smith, J. G., Organic chemistry: 6th ed.: McGraw-Hill Education, New York, 2020. Wade., L. G., Organic Chemistry: 8th ed.: Pearson Education, Inc., United States, 2013.
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