3, 4-Dihydroxyphenylacetaldehyde (DOPAL) is an important intermediate metabolite found in catecholamine neurotransmitter systems. As such, it has an important role in medicinal research directed toward the study of alcoholism, Alzheimer’s disease and Parkinson’s disease. Despite the immense biochemical significance of DOPAL, attempts to synthesize this compound in pure form has been met with grave difficulty. Various preparations of DOPAL have been reported, but the synthesis of this eight-carbon compound suffers from detailed procedures, physical isolation, full chemical characterization of the product/intermediates and extremely low overall product yield. These published methods also share one common problem, DOPAL is very unstable and is very difficult to isolate and work with. Therefore, considerable effort to produce DOPAL in a higher yield would be of interest. In an effort to mitigate these problems, we have directed our attention toward the synthesis of DOPAL using organobarium reagents. These novel reagents, fundamental to organic synthesis were utilized in the total synthesis of DOPAL. In addition, we also report the synthesis of the protected DOPAL via a Wittig reaction, but results of the hydrolysis/de-protection protocols have been interesting but unsatisfactory in the isolation of the free aldehyde. These studies may provide important insight on future drug action to combat PD and, when the scope of this research is expanded, may aid in the treatment of other neurodegenerative disorders.

Efforts toward the synthesis of 3,4-dihydroxyphenylacetaldehyde (DOPAL): A potential endogenous neurotoxin that may play a role in the development of Parkinson's disease

2019 Spring National Meeting

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