Rimantadine was among the first antiviral drugs to be licensed in the United States

Chapter 7, Problem 7.19

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Rimantadine was among the first antiviral drugs to be licensed in the United States touse against the influenza A virus and to treat established illnesses. It is synthesized fromadamantane by the following sequence (we discuss the chemistry of Step 1 in Chapter 8and the chemistry of Step 5 in Section 16.8A). Rimantadine is thought to exert its antiviral effect by blocking a late stage in the assemblyof the virus.(a) Propose a mechanism for Step 2. Hint: As we shall see in Section 22.1C, reactionof a bromoalkane such as 1-bromoadamantane with aluminum bromide (a Lewis acid, Section 4.7) results in the formation of a carbocation and AlBr42. Assumethat adamantyl cation is formed in Step 2 and proceed from there to describe amechanism.(b) Account for the regioselectivity of carbon-carbon bond formation in Step 2.(c) Describe experimental conditions to bring about Step 3.(d) Describe experimental conditions to bring about Step 4.