The phenolic methyl ether is then cleaved using the lewis acid BBr 3 . Coupling of the resulting phenol with ethyl bromoacetate is then followed by hydrolysis to yield Sulotroban. Coniferin is an important metabolite in conifers, serving as an important intermediate in cell wall lignification, as well as having other biological roles. Last year a French group reported an elagent synthesis of this compound starting from vanillin. After unmasking the aldehyde, and reduction to the alcohol, the acetates are removed with methoxide to afford the desired coniferin.
Dopamine is an important neurotransmitter.
For example, cocaine acts by blocking dopamine uptake, while a deficiency of dopamine is associated with Parkinson s disease. Reduction to the amine, followed by reaction with 4-methoxyphenylacetyl chloride gives a compound that can be cyclized using POCl 3 . Frontalin is an aggregation pheromone of the Southern Pine Beetle. It possesses an interesting tricyclic structure containing an acetal linkage. Unfortunately, the second step in which a tosylate is displaced by an anion formed from ethyl acetoacetate does not work well.