Chapter 22, Problem 74P

Fluvastatin, a cholesterol-lowering drug, can be prepared by thefollowing three-step reaction sequence. Identify intermediates A and Band the final product, fluvastatin.

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.

The following intermediate was needed for the synthesis of tamoxifen, a widely used antiestrogen drug for treating estrogen-dependent cancers such as breast and ovarian cancer. Needed for the (A) synthesis of tamoxifen Propose a synthesis for this intermediate from compound A.

The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?

Minoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction.

The compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.

Propose a mechanism for the following reaction, an important step in the laboratory synthesis of proteins:

Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.

Identify M in the following reaction sequence used to prepare theantiulcer drug omeprazole (trade name Prilosec).