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- Select all possible products of the following questionD is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used to treat type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions.The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Draw the structure of each intermediate. Explain why a racemic product is formed.
- Slow addition of organolithium reagent A to B afforded C, anintermediate in the synthesis of the chapter-opening molecule,resiniferatoxin. Draw a stepwise mechanism for this process.Suzuki coupling of aryl iodide A and vinylborane B affords compound C,which is converted to D in the presence of aqueous acid. Identifycompounds C and D and draw a stepwise mechanism for the conversionof C to D.Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 18.34). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.
- Identify C and D in the following reaction scheme, two steps in the synthesis of the cholesterol-lowering drug atorvastatin (trade name Lipitor).Muscalure, the sex pheromone of the common housey, can be prepared by a reaction sequence that uses two nucleophilic substitutions. Identify compounds A–D in the following synthesis of muscalure.Bromoetherification, the addition of the elements of Br and OR to adouble bond, is a common method for constructing rings containingoxygen atoms. This reaction has been used in the synthesis of thepolyether antibiotic monensin (Problem 18.34). Draw a stepwisemechanism for the following intramolecular bromoetherification reaction.
- Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.An allylic alcohol contains an OH group on a carbon atom adjacent to aC—C double bond. Treatment of allylic alcohol A with HCl forms amixture of two allylic chlorides, B and C. Draw a stepwise mechanismthat illustrates how both products are formed.Muscalure, the sex pheromone of the common housefly, can be prepared by a reaction sequence that uses two nucleophilic substitutions. Identify compounds A–D in the following synthesis of muscalure.