Date of Defense
John Montgomery, Wayne State University
Steve Bertman, Chemistry
Joseph Reish, Lee Honors College
Pentalenic acid, alternative routes to pentalenic acid
Pentalenic acid is a very important molecule because it is a biosynthetic intermediate of pentalenolactone, which has antibiotic effects on Grampositive/ negative bacteria and pathogenic fungi. These effects are due to its ability to inhibit glyceraldehyde 3-phosphate dehydrogenase.1 However, the total synthesis of pentalenic acid is very lengthy.2 This project will begin the process of finding a more convenient route to pentalenic acid. Previously in this laboratory there have been experiments conducted in the cyclization of enones with nickel (0)3 It is hypothesized that this method can be used to shorten the preparation of pentalenic acid. As illustrated by the procedure taken from Crimmins and Deloach, the total synthesis of pentalenic acid is very lengthy. Scheme 2 shows this process up to a key intermediate in the synthesis 20. This is the compound the nickel chemistry will produce, and the remaining procedure will be identical to that of Crimmins and Deloach. The outline of the original synthesis along with the outline of the proposed nickel based synthesis included later will show a direct comparison of the difference in length of the two procedures.
Schlosser, Kevin, "Nickel Catalyzed Cyclizations of Alkynyl-Etones and Their Application to the Formal Synthesis of Pentalenic Acid" (1996). Honors Theses. 727.
Honors Thesis-Open Access