CHEM 343 Final Problem Set Key The first part of the problem set is brought to you by R B Woodward and William D ering s 1944 synthesis of quinine You ll feel your malaria symptoms lessening just by looking at it O H NH 2 N OEt H H 1 MeI HCl EtOH HN 2 wet Ag2O OH H O O O H O Cl HN K 2CO3 OEt H N OEt H O O OEt MeO OEt H O N N O OEt MeO O N NH H 2SO 4 O MeO N O The remainder of the problem set is comprised of R B Woodward s 1956 synthesis of lysergic acid The final steps are not included in his synthesis but are there to complete corresponding dimethyl amide Enjoy O O Cl OH Ph SOCl2 N N Ph N O O O AlCl3 N Ph O The next bit falls outside our purview so we ll rejoin the synthesis at a later point H O OH NaBH 4 mCPBA H work up N N Ph Ph O O OH O HO MeHN O OH N O O O NaIO 4 N N Ph Ph O O O N O O O H H 2O N HN Ph O O NMe LDA 78o NaBH 4 H work up H work up HN O N Cl OH OH O NMe O NMe NMe SOCl2 O N N HN N O O CN O NaCN NMe OH H H 2O NMe N HN O The final oxidation to lysergic acid is again further afield than where we need to travel so we will skip ahead to finishing the synthesis O NMe HN lysergic acid O OH 1 SOCl2 pyridine 2 NHMe 2 NMe 2 NMe HN
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