Total synthesis of plant-derived phenolic natural productsTools Simpson, Brittany (2020) Total synthesis of plant-derived phenolic natural products. MRes thesis, University of Nottingham.
AbstractNeolignans are a family of natural products that make up the active species of traditional Chinese and Japanese medicines. The understanding of the medicinal properties has led to various studies on its effect on therapeutic areas such as neurodegeneration and inflammation. This promising biological activity has led to the development of novel routes to both natural and unnatural derivatives of neolignans. Previous chemistry has been adapted to synthesize plant-derived phenolic natural products that have shown neurological activity. This thesis describes studies toward the synthesis of clovanedunnianol beginning from commercially available �-caryophyllene oxide and 4-chlorophenol. After an epoxide rearrangement and the attachment of the substituted phenol, alcohol protection and a dibromination complete the first four steps of the synthesis. In the second part of this thesis, we describe the analysis of NMR spectroscopic data for Simonsol F through calculations of 13C NMR chemical shifts using Spartan ‘18 Parallel Suite (Macintosh) software. After applying a simple scaling method, 13C NMR chemical shifts were calculated and corrected, resulting in a positive approach for confirming the assignment of Illicium simonsii-derived natural products.
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