Chapter 14, Problem 75P

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.

Fill in the missing reagents a-e in the following scheme:

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.

Identify the reagents represented by the letters a-e in the following scheme:

Draw a stepwise mechanism for the conversion of lactone C to carboxylic acid D. C is a key intermediate in the synthesis of prostaglandins by Nobel Laureate E. J. Corey and coworkers at Harvard University.

Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.

What neutral nucleophile is needed to convert dihalide A to ticlopidine, an antiplatelet drug used to reduce the risk of strokes?

Identify compounds A and B, two synthetic intermediates in the 1979 synthesis of the plant growth hormone gibberellic acid by Corey and Smith. Gibberellic acid induces cell division and elongation, thus making plants tall and leaves large.

Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants.