UC Irvine

The thesis describes two desymmetrization approaches to two different natural products. The first chapter contains background on the salvileucalins and the Buchner reaction along with the work done towards the synthesis of salvileucalin B. This includes the synthesis of the diazo substrates for the Buchner reaction and the results of experimentation on a key Buchner reaction step in the sequence. The second chapter contains background on emetine and the work done towards its synthesis. This includes the synthesis of the dihydropyridine intermediate, the results of experimentation on the key step of acidic hydrolysis of the dihydropyridine to facilitate a double Pictet–Spengler reaction, exploration of an oxidative cleavage strategy, and the results on a model system to find conditions for a successful Pictet–Spengler reaction. Future directions of the project are also discussed, which include a Mukaiyama hydration strategy and modulation of the groups on the dihydropyridine nitrogen.