“Neoprofen” is a neopentylene ring-fused one-carbon homologue analogue of ibuprofen, a well-known commercially available drug that is used for treating pain, fever, and inflammation. The neopentylene fusion is a rigid, topologically unique and hydrophobic cyclic framework feature that can provide advantages in drug discovery. Installation of the neopentylene ring fusion is also an important challenge in natural products and other target-oriented synthesis contexts. The goal of this project is to develop an improved synthesis of “neoprofen” in terms of cost, scalability, and overall efficiency by leveraging previous Dudley lab methodology for the synthesis and fragmentation reactions of vinylogous acyl nonaflates (VANs). In comparison to their triflate counterparts, nonaflates are generally cheaper and more stable. The particular nonaflates involved in this project also proved to be crystalline. Due to these factors, nonaflates have proven to be both convenient and efficient relative to triflates. The integration of these observations into other synthetic efforts is expected to advance chemical synthesis and impact future medicinal chemistry efforts.

Improved synthesis of “neoprofen”, a rigidified analogue of ibuprofen

2019 Spring National Meeting

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