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Week 5-July 29 - Week 5 Tandem Reactions The Robinson...

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Week 5 July 29, 2011 Tandem Reactions: The Robinson Annulation A remarkable tandem reaction is the Robinson Annulation , which is incredibly useful for making 6-membered rings. Provide a complete curved-arrow mechanism: + O NaOEt, EtOH O O O O Reading : Section 22.8 113
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Week 5 July 29, 2011 Retrosynthetic Analysis of the Robinson Annulation For each of the following products, show how that product could be formed via a Robinson annulation: O O OMe O O Reading : Section 22.8 114
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Week 5 July 29, 2011 The Most Important C–C Bond Formed on the Planet Provide a complete curved-arrow mechanism for the following transformation. Why is this reaction important? O OPO 3 H OH HO 3 PO OH Ribulose 1,5-bisphosphate (RuBP) O HO 3 PO OH O O OPO 3 H OH O + 2 molecules of 3-phosphoglycerate CO 2 Enzyme (base) 115
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Week 5 July 29, 2011 Test Yourself Now Provide a multistep synthesis; you may use any organic or inorganic reagents: Starting material: Desired product O OEt O O 116
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1 . Provide a synthesis for the desired product. You may use any inorganic or
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