Chemoselectivity and Protecting Groups: Crash Course Organic Chemistry #33
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Things have been getting more and more complicated here in Crash Course Organic Chemistry, 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 protecting groups, which act like a chemical disguise and help us control how molecules react. In this episode, we-ll look at what makes a good protecting group, as well as identify some good protecting groups for different functional groups. We-ll also see what role protecting groups 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 Date: 2022-04-04
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