Total Synthesis and Stereochemical Revision of Ciliatamides A-C, Total Synthesis of 8-epi-Lucentamycin A, and Development of Microwave Methodology to Facilitate the Synthesis of BMP Inhibitors

Abstract

This dissertation describes advances in total synthesis, synthetic methodology, and chemical biology. The total synthesis and stereochemical revision of Ciliatamides A-C will be discussed in detail. Also, the total synthesis of 8-epi-Lucentamycin A will be described. Lastly discussed is the development of microwave methodology to improve the synthesis of pyrazolo[1,5-a]pyrimidines. This new methodology was used to rapidly optimize a lead pyrazolo[1,5-a]pyrimidine screening hit into a highly selective and potent bone morphogenetic protein (BMP) inhibitor as well as selective KDR inhibitors using zebrafish as an in vivo screening tool.